Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
Claims 1-16 of N. Auner, et al., 17/926,842 (11/21/2022) are pending. Claims 3-4,6 and 10-13 are withdrawn as not reading on the elected species. Claims 1-2,5,7-9 and 14-16 are under examination on merits and are rejected.
Election/Restrictions
Pursuant to the election of species requirement, Applicant elected, without traverse, in the reply filed on 02/13/2026 the follows species for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable.
The elected species of the method for producing a bifunctional monosilane intermediate of the general formula (II) SiR1R21HCI:redistribution reaction of an organoperchloromonosilane of the general formula (III) SiR1R22Cl2 with an organoperhydridomonosilane of the general formula (IV) SiR1R23H2 (IV);
The elected species of the compound of formula (I): MeSiBu2Hept;
The elected species of the compound of formula (II): MeSiBuHCl;
The elected species of the compound of formula (III): MeSiBuCl2;
The elected species of the compound of formula (IV): MeSiBuH2;
The elected species of the compound of formula (V): MeSiBu2Cl;
The elected species of the compound of formula (VI): MeSiBu2H;
Claims 1-2,5,7-9 and 14-16 read on the elected species, claims 3-4,6 and 10-13 are withdrawn as not read on the elected species. The elected species are not patentable as discussed in the 103 rejection below; searching has been extended other compounds as mentioned in the 103 rejection below. The provisional species election requirement is in effect.
Claim Interpretation
During examination, a claim must be given its broadest reasonable interpretation consistent with the specification as it would be interpreted by one of ordinary skill in the art. MPEP § 2173.01(I); § 2111.01. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. The plain meaning of a term means the ordinary and customary meaning given to the term by those of ordinary skill in the art at the time of the invention. MPEP § 2173.01(I).
Summary of the Claimed Invention
The claims are directed to process for the production of silahydrocarbons of the general formula (I) SiR1R2R3R4 (I) and the independent claim 1 is schematically summarized by the Examiner as follows:
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Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Pursuant to 35 U.S.C. 112, the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000). The meaning of every term used in a claim should be apparent from the prior art or from the specification and drawings at the time the application is filed. Claim language may not be ambiguous, vague, incoherent, opaque, or otherwise unclear in describing and defining the claimed invention. MPEP § 2173.05(a).
Improper Preferences in a Claim
Claims 1-2,5,7-9 and 14-16 are rejected under 35 U.S.C. 112(b) as being indefinite for multiple recitations of the exemplary claim language “preferably”. These recitations improperly provide for preferences within a claim and thereby renders confusion over the intended scope. See MPEP § 2173.05(d). This rejection can be obviated by amending claim to remove “preferably”.
Unclear Active Steps
Claims 1-2,5,7-9 and 14-16 are rejected under 35 U.S.C. 112(b) as being indefinite because the recited active steps in claim 1 is not clear. The instant claim 1 first recites that the claimed method must comprise the step of a:
a) at least one step of producing a bifunctional monosilane intermediate of the general formula (II) SiR1R21HCI ;
The instant claim 1 further recites that the claimed method must comprise the step of b:
b) at least one step of submitting a bifunctional monosilane intermediate of the general formula (II) as obtained from step (a) or HSiCI3 to a metal-catalyzed hydrosilylation reaction with a compound containing at least one C-C double or C-C triple bond to obtain an intermediate of the general formula (V) SiR1R2R31CI.
Thus, looks like when HSiCI3 was used for the claimed metal-catalyzed hydrosilylation reaction, the recited step a) is not required to conduct the claimed method, therefore, it is not clear whether the step a) is require or not for the claimed method. There is a similar issue for the claimed step b).
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
35 USC § 103 Rejection over Onopchenko, Amin and Bakshi
Claims 1-2,5,7,9 and 14-16 are rejected under 35 U.S.C. 103 as being unpatentable over a combination of A. Onopchenko, et al, . 52(18), The Journal of Organic Chemistry, 4118-4121(1987)(“Onopchenko”); S. B. Amin, et al, 129(10), Journal of the American Chemical Society 2938-2953 (2007)(“Amin”) and K. R. Bakshi, et al, US 4595777 (1986)(“Bakshi”).
A. Onopchenko, et al, 52(18), The Journal of Organic Chemistry, 4118-4121(1987)(“Onopchenko”)
Onopchenko teaches a process for the production of hexyltrioctylsilane as follows:
Reaction of n-Hexylsilane with 1-Octene. A 100-mL, three-necked, round-bottomed flask, fitted with a condenser connected to a nitrogen source, a stirrer, thermometer, and a serum cap, was charged with 1-octene (10.0 g, 89 mmol), n-hexylsilane (1.4 g, 12.1 mmol), and chloroplatinic acid hexahydrate (0.004 g, 7.7 x 10-3 mmol). After being purged with nitrogen (15 min), the mixture was heated to 95 °C. After 1 h, the reaction stopped at about 50% silane conversion. The mixture was cooled to 25 °C, and compressed air was bubbled vigorously through the mixture for 1 min. The mixture was again heated to 95 °C (under N2) for 1 h. Analysis (GLC) showed that silane completely reacted to give hexyltrioctylsilane . . . ..
Onopchenko at page 4121, left col. Experimental, Reaction of n-Hexylsilane with 1-Octene, emphasis added.
Examiner schematically summarize the Onopchenko method as:
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Which maps the step d as:
The R1SiH3 is n-Hexylsilane, wherein R1 is n-hexyl that is a alkyl;
The compound containing one or more C-C double bonds or C-C triple bonds is1-octene; and
The SiR1R2R3R4 is hexyltrioctylsilane, wherein R1 is n-hexyl and each of R2-R4 is octyl.
Difference Between Onopchenko and the Claims
Onopchenko differs from the instant claim 1 only in that it does not teaches to prepare n-hexylsilane by a hydrogenation reaction of n-hexyltrichlorosilane.
S. B. Amin, et al, 129(10), Journal of the American Chemical Society 2938-2953 (2007)(“Amin”)
Amin teaches a method of preparing of n-hexylsilane from n-hexyltrichlorosilane in the presence of LiAlH4 and tetraglyme with an yield of 92%. Amin at supporting information, page S9, Synthesis of n-hexylsilane.
Thus, Amin teaches a method of preparing of n-Hexylsilane by a hydrogenation reaction of n-hexyltrichlorosilane.
K. R. Bakshi, et al, US 4595777 (1986)(“Bakshi”)
Bakshi teaches that
Tetraalkyl substituted silanes have been proposed for use in the formulation of hydraulic fluids and lubricants since they possess excellent viscosities over a wide temperature range and low pour points in addition to excellent thermal stability.
Bakshi at col. 1, line 19-23.
Bakshi teaches that desired tetraalkylsilane product has the general formula of
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Wherein,
R is an alkyl radical containing from one to twenty carbon atoms per molecule; and
R1, R2 and R3 are the same or different and represent alkyl radicals containing from six to twenty carbon atoms per molecule.
Therefore, one ordinary skill would be appraised that the Onopchenko hexyltrioctylsilane is a species of the Bakshi tetraalkyl substituted silanes; and it can be used as hydraulic fluids and lubricants. Thus, Bakshi teaches motivation to synthesis of the Onopchenko hexyltrioctylsilane.
Obviousness Rationales of Claims 1-2,5,7,9 and 14-16
Claim 1 is obvious because one ordinary skill seeking the Onopchenko hexyltrioctylsilane as hydraulic fluids and lubricants is motivated to use the Amin method to prepare n-Hexylsilane by a hydrogenation reaction of n-hexyltrichlorosilane and use the Onopchenko method to prepare hexyltrioctylsilane as indicated below, thus arrive at a method meeting each and every limitation of claim 1, therefore, claim 1 is obvious.
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One ordinary skill has a motivation to do so with a reasonable expectation of success because:
(i). Bakshi teaches that Onopchenko hexyltrioctylsilane can be used as hydraulic fluids and lubricants;
(ii). Onopchenko teaches that hexyltrioctylsilane can be prepared through reacting of n-Hexylsilane with 1-octene in the presence of chloroplatinic acid hexahydrate as catalyst; and
(ii). Amin teaches a method of preparing of n-Hexylsilane by a hydrogenation reaction of n-hexyltrichlorosilane.
Rationales supporting the modification is combining prior art elements according to known methods to yield predictable results. MPEP 2143. I. (A).
Claims 2 and 5 are obvious because hexyltrioctylsilane comprise n-hexyl and octyl two different groups, both of which is saturated hydrocarbon groups.
Claims 7-9 and 14-15 are obvious because the proposed method is an alternative of step a, b and c of hydrogenation of the general formula (V) formed in step b that is the proposed method does not require steps a and b.
Claim 16 is obvious because chloroplatinic acid hexahydrate is a Pt based catalyst.
35 USC § 103 Rejection over a Combination of Leguijt and. Saxena, Takeshi, Oertle and Mautner
Claims 1-2,5,7-9 and 14-16 and the elected species are rejected under 35 U.S.C. 103 as being unpatentable over a combination of R. Leguijt, et al, US 2015/0370062 A1 (2015)(“Leguijt”), K. Saxena, et al, 23(12), Applied Organometallic Chemistry, 535-540(2009)(“Saxena”), ABE Takeshi, et al, JP2017160160A (2017)(“Takeshi”), K. Oertle, et al, 26(45), Tetrahedron Letters, 5511-5514 (1985)(“Oertle”) and K. Mautner, et al, US 20110196165A1 (2011)(“ Mautner”).
R. Leguijt, et al, US 2015/0370062 A1 (2015) (“Leguijt”)
Leguijt teaches an electrowetting apparatus including at least one compound selected from the group consisting of:
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wherein each of R1, R2, R3 and R4 is independently an alkyl group. Leguijt at abstract.
Leguijt teaches that the alkyl group of each of R1, R2, R3 and R4 is a straight chain, i.e. unbranched, alkyl group having the general formula -(CH2)nCH3 where n is independently, for each of R1, R2, R3 and R4, in the range of 0 to 7. Leguijt at page 5, [0050], line 1-4, emphasis added.
Leguijt teaches example compounds such as Example 3 and Example 5 having a structure as indicated below. Leguijt at page 5, Example 3 and page 6, Example 5.
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One of ordinary skill is motivated to select the Leguijt Example 3 for further investigation because Leguijt discloses it as an example of his compounds and it can be used as a to manufacture an electrowetting apparatus. Having selected the Leguijt Example 3, one of ordinary skill is motivated to substitute the one of n-butyl groups with a methyl groups as follows.
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One ordinary skill has a motivation to do so with a reasonable expectation of success because per Example 5, Leguijt teaches that his compound can comprise one methyl group.
Given dibutymethylsilane [MeSiBu2H that is the elected species of the compound of formula (VI)] is an often used building block for hydrosilylation of Si-H bearing organosilicon with compound containing one or more C-C double bonds in the presence of a Pt based catalyst, [See. Saxena, et al, 23(12), Applied Organometallic Chemistry, 535-540(2009)(“Saxena”) scheme 1 at page 538; V.V. Kovalenko, et al, (3), Vestnik BGU, et al, Biologiya, Geografiya 34-38 (2008)(“Kovalenko”), see the attached CA abstract],
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one ordinary skill is motivated to utilize dibutymethylsilane as a starting material to react with 1-butene as indicated below.
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The above proposed method meets each and every limitation of the step d in claims 1, 2,5 and 16.
Difference Between Combination of Leguijt and Saxena and the Claims
The combination differs from the claim 1 in that it does not teach the claimed method to prepare the intermediate of MeSiBu2H, however, the following secondary art teaches a method to prepare the intermediate of MeSiBu2H.
The Second Art: ABE Takeshi, et al ,JP2017160160A (2017)(“Takeshi”).
Takeshi is published in Japanese and a copy of machine translation is attached as the second part of the reference, which results the full reference has 20 pages. The format for recitation of the reference is xx/20.
Takeshi teaches a method for producing a silicon hydride compound by converting a silicon-halogen bond to a silicon-hydrogen bond using a boron hydride. Takeshi at [0001]
Takeshi teaches working examples for his method such as the follows Example 3.
Synthesis Example 3 After replacing the interior of a 7 mL test tube equipped with a stirring bar with nitrogen gas, 0.5 mL of acetonitrile as a reaction solvent and 0.5 mL of a reducing agent (manufactured by Sigma-Aldrich Japan Co., Ltd. 37.8 mg (1.0 mmol) of sodium borohydride (NaBH4, Reagent Plus (registered trademark), purity 99%) were added to prepare a suspension. To this suspension, 83.9 μL (0.5 mmol) of triethylchlorosilane (Et3SiCl) was dropped using a microsyringe, and the mixture was allowed to react for 15 minutes while stirring at room temperature. After the reaction, 18.6 mg (0.1 mmol) of ferrocene was added as a reference substance for calculating the NMR yield. A part of the obtained mixed solution was dissolved in deuterochloroform (CDCl3) and 1H NMR was measured. As a result, triethylsilane (Et3SiH) was produced with an NMR yield of 88%.
Takeshi at page 18/20, [0041], Synthesis Example 3, emphasis added.
Examiner schematically summarize the Takeshi Example 3 method as:
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To conduct the synthesis of the above proposed tributyl(methyl)silane, one ordinary skill has a motivation to utilize the Takeshi Example 3 method to prepare of the intermediate of MeSiBu2H through MeSiBu2Cl1 [ the elected species of the compound of formula (V)] as indicate below, which meets each and every limitation of the step c in claims 1 and 15.
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MeSiBu2Cl and Et3SiCl are homologs. Compounds which are homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. Thus, one ordinary skill has a reasonable expectation of success.
The Second Arts: K. Oertle, et al, 26(45), Tetrahedron Letters, 5511-5514 (1985)(“ Oertle”).
Oertle teaches that MeSiBuHCl [the elected species of the compound of formula (II)] is a building blocks for hydrosilylation of olefins. Oertle at page 5512, Table 1, Enty 5.
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Oertle also teaches that Hydrosilylation of olefins is known to proceed under a great variety of reaction conditions. The process is initiated not only thermally but also with catalysts such as radical initiators, bases, Lewis acids (e.g. BCl3, B(OH)3, AlCl3) or transition metals (eg. Ni, Pd, Pt, Co, Rh, Ir). Oertle at page 5511, last paragraph.
To conduct the synthesis of the above proposed tributyl(methyl)silane, one ordinary skill has a motivation to utilize the Oertle MeSiBuHCl as a starting material to react with 1-butene to synthesis of MeSiBu2Cl as indicated below.
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which meets each and every limitation of the step b in claims 1 and 14.
K. Mautner, et al, US 20110196165A1 (2011)(“Mautner”)
Mautner teaches:
[0005]a process for preparing silanes of the general formula (1)
RaHbSiCl4−a−b (1)
in which mixtures of silanes of the general formulae (2) and (3)
RcSiCl4−c (2)
RdHeSiCl4−d−e (3)
where
[0006]R is an alkyl radical having 1 to 6 carbon atoms,
a is 1, 2 or 3,
b is 0 or 1,
c is 1, 2, 3 or 4,
d is 0, 1 or 2 and
e is 0, 1 or 2,
are converted in the presence of an alumina catalyst which comprises, per 100 parts by weight of alumina, 1 to 10 parts by weight of aluminum chloride and 0.5 to parts by weight of a metal oxide selected from magnesium oxide, copper oxide, zinc oxide and mixtures thereof.
Mautner at page 1, [0005]-[0006].
After comparing the Mautner formula (1)-(3), one ordinary skill would be appraised that the Oertle MeSiBuHCl is a species of the Mautner formula (1) and it can be prepared through reacting of MeSiBuCl2 that is the elected species of the compound of formula (III) and a species of the Mautner formula (2) with MeSiBuH2 that is the elected species of the compound of formula (IV) and a species of the Mautner formula (3) as indicated below.
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which meets each and every limitation of the step a in claims 1, 7 and the elected species for preparation of the formula (II).
Obviousness Rationales of the Claims
Obviousness of a claimed compound can be supported where there is motivation to substitute particular chemical moieties in a prior art compound for others so as to arrive at a claimed compound. MPEP § 2143(I)(B). For example, in the pharmaceutical arts, the rational is stated as motivation to select a known compound and also motivation to structurally modify the selected compound in a particular way to achieve a claimed compound. MPEP § 2143(I)(B) (see for example, MPEP § 2143(I)(B) Example 9, citing Eisai Co. Ltd. v. Dr. Reddy’s Labs., Ltd., 533 F.3d 1353, 87 USPQ2d 1452 (Fed. Cir. 2008).
One of ordinary skill is motivated to select the Leguijt Example 3 for further investigation because Leguijt discloses it as an example of his compounds and it can be used as a to manufacture an electrowetting apparatus.
Having selected the Leguijt Example 3, one of ordinary skill is motivated to substitute the one of n-butyl groups with a methyl groups as follows.
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One ordinary skill has a motivation to do so with a reasonable expectation of success because per Example 5, Leguijt teaches that his compound can comprise one methyl group.
Claim 1 and the elected species of MeSiBuHCl, MeSiBuCl2, MeSiBuH2, MeSiBu2Cl as well MeSiBu2H are obvious because one ordinary skill is motivated to combine the above prior arts method to synthesize the proposed tributyl(methyl)silane:
(a). utilize the Mautner method to synthesize MeSiBuHCl through redistribution reaction between MeSiBuCl2 and MeSiBuH2,
(b). utilize the Oertle method to synthesize MeSiBu2Cl from MeSiBuHCl,
(c). utilize the Takeshi method to synthesize MeSiBu2H from MeSiBu2Cl, and
(d). utilize the Saxena/ Kovalenko method to synthesize MeSiBu3 from MeSiBu2H;
as indicated below, thus arrive at a method meeting each and every limitation of claim 1 and the said elected species, therefore claim 1 and the said elected species are obvious.
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One ordinary skill has a motivation to do so with a reasonable expectation of success because:
(i). Leguijt teaches that the above proposed tributyl(methyl)silane can be used to manufacture an electrowetting apparatus;
(ii). Saxena/ Kovalenko teaches that MeSiBu2H is an often used building block for hydrosilylation of Si-H bearing organosilicon with compound containing C=C bond to form a tetra substituted silane;
(iii).Takeshi teaches that silicon hydride compound such as MeSiBu2H can be prepared through hydrogenation of a silicon-halogen compound such as MeSiBu2Cl using a boron hydride;
(iv). Oertle teaches that MeSiBu2Cl can be prepared through hydrosilylation of 1-butene with MeSiBuHCl; and
(v). Mautner teaches that MeSiBuHCl can be prepared through reacting of MeSiBuCl2 with MeSiBuH2.
Rationales supporting the modifications is “combining prior art elements according to known methods to yield predictable results”. MPEP 2143.I(A).
Claims 2 and 5 are obvious because the proposed tributyl(methyl)silane comprise two different alky groups that are methyl and butyl group, both of which are saturated hydrocarbon groups.
Claim 7 is obvious because the MeSiBuHCl formed in the step a of the proposed method comprises methyl and butyl group, both of which are saturated hydrocarbon groups.
Claims 9 is obvious because one ordinary skill is motivated to conduct the step a of the proposed method at 180 ºC as Mautner teaches that the reaction is preferably conducted at a temperature of 180 ºC. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05. I. Herein, the claimed temperature 0-180 ºC overlaps with the prior art 180 ºC, therefore, a prima facie case of obviousness exists. The claim using “and/or” language, prior art teaches one alternative meets the claim.
Claim 14 is obvious because one ordinary skill is motivated to conduct the step b of the proposed method with a Pt based catalyst as Oertle teaches that hydrosilylation of olefins with MeSiBuHCl can be catalyzed by Pt based catalyst.
Claim 15 is obvious because one ordinary skill is motivated to conduct the step c of the proposed method with NaBH4 as the hydride agent given Takeshi teaches that NaBH4 can be used as the hydride agent for converting a silicon-halogen bond to a silicon-hydrogen bond.
Claim 16 is obvious because one ordinary skill is motivated to conduct the step d of the proposed method with a Pt based catalyst because both Saxena and Kovalenko teaches to use a Pt based catalyst for hydrosilylation of olefins with MeSiBu2H.
The elected species of MeSiBu2Hept is also obvious because one ordinary skill is also motivated to further modify the proposed compound by replacing one butyl group with heptyl group as indicated below, thus arrive at the elected species MeSiBu2Hept.
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One ordinary skill has a motivation to do so with a reasonable expectation of success because that heptyl is an alternative group of butyl group as Leguijt teaches that in his compound of
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, the alkyl group of each of R1, R2, R3 and R4 is a straight chain, i.e. unbranched, alkyl group having the general formula -(CH2)nCH3 where n is independently, for each of R1, R2, R3 and R4, in the range of 0 to 7. One ordinary skill has a motivation to synthesize MeSiBu2Hept through hydrosilylation of 1-heptene with MeSiBu2H as indicated below with a reasonable expectation of success for the same reason as given above.
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Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)2705241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 US5258535A disclose the compound of MeSiBu2Cl at col. 6, Example 4 through chlorination of MeSiBu2H.