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 .
Status of the Claims
Currently, claims 1-7 are pending in the instant application.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 08/30/2023 and 04/16/2025 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Rejections - 35 USC § 112 – First Paragraph
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-7 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 1 recites “a divalent or higher valent metal fluoride ion”. However, Applicant’s disclosure does not meet the written description requirement to claim such a metal fluoride ion. Under broadest reasonable interpretation, “a divalent or higher valent metal fluoride ion” would encompass any metal fluoride having two or more fluoride atoms. Looking towards, Applicant’s disclosure, eight exemplary synthesis procedures are provided (Specification page 22-38). In each of the provided examples, the sole metal halide ion used is silver (II) fluoride (AgF2). The sole use of AgF2 would not reasonably be representative of any and all possible divalent or higher metal fluoride ions.
Claim 1 recites “an organic salt including a quaternary ammonium cation or a quaternary phosphonium cation”. Firstly, the recitation of the word “including” does not explicitly limit the recitation of “an organic salt”. Accordingly, the recitation of “an organic salt including a quaternary ammonium cation or a quaternary phosphonium cation” would encompass any and all organic salts, and Applicant’s disclosure could not reasonably meet the written description requirement for such a wide breadth of compounds. Secondly, looking towards Applicant’s provided exemplary syntheses, (Specification page 22-38), it appears that in each of Examples 1-8, the only organic salt used is the quaternary ammonium salt of NEt4Cl. The sole use of NEt4Cl would not reasonably be representative of any and all possible quaternary ammonium and phosphonium cations.
Claims 2-5 and 7 are rejected for the same reasons as claim 1 because they inherit the limitation regarding “a divalent or higher valent metal fluoride ion”.
Claims 2-6 are rejected for the same reasons as claim 1 because they inherit the limitation regarding “an organic salt including a quaternary ammonium cation or a quaternary phosphonium cation”.
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.
Claim(s) 1-7 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ou (Journal of Fluorine Chemistry 101 (2000) 279-283) in view of Williams (WO 94/22817).
Claim 1 recites a method for producing a pentafluorosulfanyl group-containing aryl compound represented by formula (1):
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From a thioaryl compound of formula (2):
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By oxidative fluorination reaction using a divalent or higher valent metal fluoride and an organic salt including a quaternary ammonium cation or a quaternary phosphonium ion.
Ou teaches the synthesis of aryl sulfur pentafluorides. More specifically, the formation through oxidative fluorination of phenyl sulfur pentafluoride (PhSF5) by combining phenyl disulfide, xenon disulfide, and NEt4Cl, wherein the overall reaction is provide below (page 279, (2)):
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The phenyl disulfide used by Ou is a compound of formula (2) wherein A1 is phenyl (i.e., unsubstituted aryl) and G1 is S-S-R1, wherein R1 is unsubstituted aryl. The resulting product of PhSF5 is a compound of formula (1) wherein A1 is phenyl. Furthermore, Ou uses the quaternary ammonium salt NEt4Cl. In an exemplary synthesis, PhSF5 was produced at a 25% yield (page 282)1. Ou does not explicitly teach the use of a divalent or higher valent metal fluoride. However, the use of such a metal fluoride would be obvious because Ou indicates that it is known in the art that aryl sulfide pentafluorides can be formed using AgF2, and Williams teaches the use of silver difluoride (AgF2) to convert aryl disulfides to aryl sulfur pentafluorides at greater yield.
As indicated above, Ou does not explicitly teach the use of AgF2, however they do make mention that AgF2 can be used to form aryl sulfur pentafluorides (page 279)2.
Similarly to Ou, Williams teaches a method of synthesizing aryl sulfur pentafluorides from aryl disulfides. However, the teachings of Williams differ from the teachings of Ou in that Williams combines aryl disulfides with AgF2 to form the final aryl sulfur pentafluoride. The general method of Williams is provided in the diagram below (Page 12, Scheme 1):
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Williams further provides an exemplary synthesis wherein 4-nitrophenyldisulfide (50 g) is combined with AgF2 (400 g) and heated to 122-124C for 6 hours in order to form the final nitrophenyl pentasulfide (page 7)3. Williams’ synthesis provided product in 99% purity and a yield of 78% (page 7)4. As the method of Williams appears to provide a higher yield of final product, a person or ordinary skill in the art would be motivated to use AgF2 as a fluorination agent rather than the XeF2 of Ou.
It would have been prima facie obvious at the time of invention for a person of ordinary skill in the art to combine the teachings of Ou and Williams, and substitute the use of XeF2 of Ou, for the AgF2 used by Williams, because there would be a reasonable expectation that the yield of the final aryl sulfur pentafluoride product would be greater.
Claim 2 further limits the method of claim 1 wherein A1 is:
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Ou teaches PhSF5 which is a compound of formula (1) wherein A1 is unsubstituted aryl.
Claim 3 further limits the method of claim 1 wherein the oxidative fluorination reaction is carried out at -40 to 130C.
Ou teaches reaction at 25C.
Claim 4 further limits the method of claim 1 wherein a metal produced after the oxidative fluorination is recovered.
Williams teaches that AgF2 is consumed in reaction to form AgF, which can be collected and re-fluorinated into AgF2 for repeated use (pages 4-5)5.
Claim 5 further limits the method of claim 4 wherein the recovered metal is fluorinated to regenerate a divalent or higher valent metal fluoride, and the obtained divalent or higher valent metal fluoride is used again in the oxidative fluorination reaction.
As iterated in the claim 4 rejection, Williams teaches that AgF2 is consumed in reaction to form AgF, which can be collected and re-fluorinated into AgF2 for repeated use.
Claim 6 further limits the method of claim 1 wherein the divalent or higher valent metal fluoride is silver (II) fluoride.
Williams teaches the use AgF2 (silver (II) fluoride).
Claim 7 further limits the method of claim 1 wherein the organic salt is tetraalkylammonium halide.
Ou teaches the use of Net4Cl, which is a tetraalkylammonium halide.
Conclusion
Claims 1-7 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ERIC TRAN whose telephone number is (571)272-7854. The examiner can normally be reached Mon-Fri 8:00-5:00.
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/ERIC TRAN/Examiner, Art Unit 1629
/JEFFREY S LUNDGREN/Supervisory Patent Examiner, Art Unit 1629
1 “To PhSSPh (17 mg, 0.078 mmol) in CD2Cl2 (0.3 mL) in a ptfe-lined NMR tube was added Et4NCl (2 mg, 0.012 mmol) at 258C. Solid XeF2 (82 mg, 0.48 mmol) was then added slowly to the reaction mixture and the colourless solution turned yellow, with gas evolution. After 30 min, another batch of Et4NCl (6 mg, 0.036 mmol) was added. Gas evolved vigorously and the solution turned deep yellow and back to colourless, to give PhSF5 (25%), identified by 19F NMR”
2 “Arylsulfur pentafluorides have been made previously by the reaction of AgF2 with aryl disulfides or arylsulfur trifluorides”
3 “4-Nitrophenyldisulphide (50g) was charged to the reaction vessel and agitation was commenced. Silver difluoride (400g) was added in one portion to the stirred mixture at ambient temperature from a solid addition funnel designed to maintain an inert atmosphere over the contents during the charging procedure. Last traces of silver difluoride were rinsed into the reactor with (50 mls) of octane. The temperature of the reactor and contents was raised over 2 hours to 122 - 124°C and held at this temperature for 6.5 hours.”
4 “The chloroform eluents were evaporated to give 74 grams of product whose purity was estimated as 99% by HPLC whilst GC analysis indicated 16% octane/hydrocarbon content. The yield was thus 78% (based on disulphide charged and GC analysis of purity).”
5 “Silver difluoride consumed during the reaction is converted to silver fluoride which is also insoluble under the reaction conditions. Silver fluoride and any unreacted silver difluoride remaining after the reaction is complete are thus readily recovered by filtration, optionally with washing using a suitable solvent. Silver difluoride is readily re-formed by the treatment of silver fluoride with a fluorinating agent such as gaseous fluorine. Thus whilst the excess silver difluoride used in the process of the present invention represents an expensive capital outlay, the silver may be used effectively as a carrier for the fluorine used in the formation of the sulphurpentafluoride moiety and may be re-cycled repeatedly without serious loss.”