DETAILED ACTION
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 .
Drawings
The drawings were received on July 20, 2026. These drawings are acceptable.
Response to Amendment
The amendment to claims 1 and 3, submitted July 20, 2026 is acknowledge and entered.
Response to Arguments
Applicant’s arguments, see page 6, filed July 20, 2026, with respect to objection to the Specification have been fully considered and are persuasive. The objection to the Specification has been withdrawn.
Applicant’s arguments, see page 6, filed July 20, 2026, with respect to the rejection of claims 9 – 10 under 35 USC 112(b) & 101 have been fully considered and are persuasive in view of the cancellation of the claims. The rejection of claims 9 – 10 under 35 USC 112(b) has been withdrawn.
Applicant’s arguments, see page 7, filed July 20, 2026, with respect to the rejection of claim 8 under 35 USC 102(a)(1) as anticipated by Wen et al. (CN 108976248) or Chen et al. (Communications: Hypervalent compounds) or Tietze et al. (Chem. Eur. J.) have been fully considered and are persuasive in view of the cancellation of the claim 8. The rejection of claim 8 under 35 USC 102(a)(1) as anticipated in view of Wen, Chen or Tietze has been withdrawn.
Applicant’s arguments, see page 8, filed July 20, 2026, with respect to the rejection of claims 9 – 10 under 35 USC 103 have been fully considered and are persuasive in view of the cancellation of the claims. The rejection of claims 9 – 10 under 35 USC 103 has been withdrawn.
Applicant’s arguments, see page 8 – 9, filed July 20, 2026, with respect to the rejection of claims 1 - 7 under 35 USC 103 as unpatentable over Narjes et al. have been fully considered and are persuasive in view of the arguments presented and amendment to claim 1. The rejection of claims 1 - 7 under 35 USC 103 as unpatentable over Narjes et al. has been withdrawn.
Applicant's arguments filed July 20, 2026, with regard to the rejection of claims 1 – 7 under 35 USC 103 as unpatentable over Dunzhu et al have been fully considered but they are not persuasive for the reasons set out in the Office Action mailed April 20, 2026 and as set out below.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim(s) 1 – 7 are rejected under 35 U.S.C. 103 as being unpatentable over Cui Dunzhu et al. (CN 106565434) (Dunzhu) (See English translation).
The rejected claims cover, inter alia, a method for preparing a 2-iodo-aromatic ether under the action of alkali metal hydrides comprised of the following steps: reacting a 1, 2-iodo-aromatic hydrocarbon with a phenol in the presence of an alkali metal hydride to obtain the 2-iodo- aromatic ether, wherein the chemical structural formula of the 1,2-iodo-aromatic hydrocarbon is
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wherein Ar1 is benzene or naphthalene.
Dependent claims 2, 6 and 7 further limit the method. Dependent claims 3, 4 and 5 further limit the reactants.
However, Dunzhu discloses the synthesis of 1-bromo-2-phenoxy benzene from the reaction of phenol and 1-bromo-2-iodobenzene with sodium hydride.
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Take phenol 0.1mol, dissolved in 100mL of anhydrous tetrahydrofuran, stirred, accurately weighed 0.4mol sodium hydride added to the reaction batch in batches, do not be too fast, to prevent too much bubbles, after the solution was yellow, then add 1-bromo-2-iodobenzene 0.11mol (added in portions) at room temperature overnight; the resulting reaction product was filtered to remove solid material, the filtrate spin dry, dissolved in methylene chloride, the column with petroleum ether: ethyl acetate = 1: 5 (volume ratio) column to give 1-bromo-2-phenoxybenzene (Intermediate A-1) (0.05 mol, y = 50%). Mass spec: 249.97. (pp. 11).
In Example 2 the synthesis of intermediates A-5 and A-6 were prepared in the same molar ratio according to Example 1 above. Table 1, reproduced in-part below, shows the reaction material and resulting products.
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The difference between the instantly claimed invention and Dunzhu is as follows: the instantly claim invention has as reactant 1,2-diiodoarene and as product 2-iodoaryl ether; the mole ratio of phenol to the 1,2-iodo-aromatic hydrocarbon to the alkali metal hydride; and the reaction time or 0.2-10 hours.
However, with regard to the instantly claim invention having as reactant 1,2-diiodoarene and as product 2-iodoaryl ether and Dunzhu’s reactant being 1-bromo-2-phenoxy benzene and product being 1-bromo-2-phenoxybenzene; the Examiner notes that both solve the problem of providing a process for the preparation of 2-haloaryl ethers. With regard to the distinction between the halogens, iodine and bromine are similar in nature and are both commonly known halogens in the art. Also, one of ordinary skill in the art would readily recognize that the reaction starting material could be substituted from 1-bromo-2-iodobenzene to 1,2-diiodo benzene to prepare other commonly known 2-haloaryl ethers.
Because each of the references teach methods for the preparation of 2-haloaryl ethers, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instantly claimed invention to substitute iodine for the bromine in the 1-bromo-2-iodobenzene to prepare 2-iodo-aromatic ether by the process of Dunzhu to achieve the predictable result of preparing 2-iodo-aromatic ether.
Therefore, the claims would have been obvious because the substitution of one known element for another would have yielded predictable results to one of ordinary skill in the art at the time of the invention. KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385 (U.S. 2007).
Regarding claim 2, Dunzhu in Example 1 discloses the phenol dissolved in anhydrous tetrahydrofuran, stirred, and sodium hydride added to the reaction batch in batches. As such this limitation is deemed to be obvious absent a showing of unexpected results.
A reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings. (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976). In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35USC 103.
Regarding claim 3, Dunzhu discloses the use of the solvent tetrahydrofuran in Examples 1 and 2. As such this limitation is deemed to be obvious.
Regarding claim 4, Examples 1 and 2 of Dunzhu discloses the use of sodium hydride. As such this limitation is deemed to be obvious.
Regarding claim 5, Example 1 of Dunzhu discloses the phenol reactant and Table 1 discloses a heterocyclic phenol as a reactant.
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. As such this limitation is deemed to be obvious.
Regarding claim 7 and the temperature set out therein, Example 1 of Dunzhu discloses that the reaction takes place at room temperature. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. (In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976)) (MPEP 2144.05 I.)
Regarding claim 6 molar ratio, and claim 7 reaction time, based on the teaching of Dunzhu these limitations can easily be determined by routine experimentation. Noting that in Example 1 the reaction takes place over night. Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." (In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955)) (MPEP 2144.05 II. A.)
Applicant’s Arguments
In addition to the amendment to claim 1, Applicant respectfully asserts benzene or naphthalene." The present application further discloses that "[t]he preparation method of the 2-iodo-aromatic ether of the present invention has the following advantages: 1) transition metal catalysts are not needed to be added in the coupling process, so that metal pollution to products is avoided; 2) the method can be carried out at room temperature, it has high functional group compatibility, and it solves the problem that the coupling reaction of the existing metal catalysis into the aromatic ether needs to be carried out at higher temperature; 3) the reaction is simple, the reagent is cheap, and the required cost is low; 4) it can prepare the products that are not easily prepared by other methods, such as products with iodine in both aromatic rings." Specification, page 3, lines 7-16.
In response the Examiner states the following. With regard to 1) transition metal catalysts are not needed to be added in the coupling process, so that metal pollution to products is avoided.” Examples 1 and 2 of Dunzhu does not discloses the use of a transition metal catalyst. With regard to; 2) the method can be carried out at room temperature. Examples 1 and 2 of Dunzhu is conducted at room temperature. Regarding 3) the reaction is simple, the reagent is cheap, and the required cost is low. Dunzhu basically has the same reactants. The difference is being the distinction between the iodine and bromine on the benzene ring. As previously stated, iodine and bromine are similar in nature and are both commonly known halogens in the art. Also, one of ordinary skill in the art, before the effective filing date of the instantly claimed invention, would readily recognize that the reaction starting material could be substituted from 1-bromo-2-iodobenzene to 1,2-diiodo benzene to prepare other commonly known 2-haloaryl ethers.
Regarding 4) it can prepare the products that are not easily prepared by other methods, such as products with iodine in both aromatic rings; the feature is not claimed. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993) (Claims to a superconducting magnet which generates a "uniform magnetic field" were not limited to the degree of magnetic field uniformity required for Nuclear Magnetic Resonance (NMR) imaging. Although the specification disclosed that the claimed magnet may be used in an NMR apparatus, the claims were not so limited.); Constant v. Advanced Micro-Devices, Inc., 848 F.2d 1560, 1571-72, 7 USPQ2d 1057, 1064-1065 (Fed. Cir.), cert. denied, 488 U.S. 892 (1988) (Various limitations on which appellant relied were not stated in the claims; the specification did not provide evidence indicating these limitations must be read into the claims to give meaning to the disputed terms.); Ex parte McCullough, 7 USPQ2d 1889, 1891 (Bd. Pat. App. & Inter. 1987) (Claimed electrode was rejected as obvious despite assertions that electrode functions differently than would be expected when used in nonaqueous battery since "although the demonstrated results may be germane to the patentability of a battery containing appellant’s electrode, they are not germane to the patentability of the invention claimed on appeal."). (MPEP 2145, VI).
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to YATE' K. CUTLIFF whose telephone number is (571)272-9067. The examiner can normally be reached Monday-Friday (8:30 - 5:30).
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Y. Goon can be reached at (571) 270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/YATE' K CUTLIFF/Primary Examiner, Art Unit 1692
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