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 .
Claim Status
Claims 1 and 12-20 were amended and claims 8 and 11 were canceled in the response filed 8/17/2026. Claims 1-7, 9-10, 12-20, and 22 are pending. Claims 1-7, 9-10, and 22 stand withdrawn. Claims 12-20 are under examination.
Withdrawn Objections and Rejections
The amendments filed on 8/17/2026 are persuasive to overcome the objection to the specification of record on p. 3 of the OA dated 5/18/2026; therefore, the objection is withdrawn.
The amendments to the claims filed on 8/17/2026 are persuasive to overcome the 35 USC 112(b) rejection of record on p. 3-4 of the OA date 5/18/2026. By amending the dependency of the dependent claims to depend from claim 12, the antecedent basis issues have been corrected. Therefore, the rejection is withdrawn.
The Applicant canceled claim 11 and amended dependent claims 13-20 to depend from claim 12. Therefore the 35 USC 102(a)(1) rejections of record over:
Adachi (JP2006151894A, published on 6/15/2006, including translation thereof) on p. 6-7 of the previous OA;
Kunigami (“Synthesis of fluoromethyl ethers and fluoromethyl esters by the reaction of the corresponding methylthiomethyl ethers and methylthiomethyl esters with IF5-pyridine-HF” Journal of Fluorine Chemistry, 2014, p. 101, of record in the IDS filed on 4/25/2023) on p. 8 of the previous OA;
Stevens (“Fluorination of Some Nitriles and Ketones with Bromine Trifluoride” J. Org. Chem, 1961, p. 1627) as evidenced by Osborne (full citation above) and Acetonitrile on p. 8-9 of the previous OA; and
Ayuba (“Selective trifluorination of alkyl aryl sulfides using IF5”, Tetrahedron, 2004, p. 11445, of record in the IDS filed on 11/6/2024) as evidenced by Osborne (full citation above) and Dichloromethane on p. 9 of the previous OA;
are withdrawn because none of the rejections included independent claim 12.
The Applicant canceled claim 11 and amended the concentration in independent claim 12 to require a concentration of 3.5 or mole per liter of the IF5 in the organic solvent. Therefore, the 35 USC 102(a)(1) rejection of record over Engel (“Photolysis of Azoalkanes. Reactions and Kinetics of the 1-Cyclopropylcyclopentane-1,3-diyl Biradical and the 1-cyclopropylcyclopentyl Radical” J. Am. Chem. Soc. 1991, p. 2686) as evidenced by Osborne and Dichloromethane on p. 7 of the previous OA is withdrawn because the reference only teaches a single concentration of 2.8 mol per liter.
Notes for Calculations and Conversions in Prior Art Rejections
Osborne (Calorimetric Study of Iodine Pentafluoride: Heat Capacity between 5 and 350°K, Enthalpy of Fusion and Vaporization, Standard Entropy of the Vapor, and Other Thermodynamic Properties” J. Chem. Phys, 1971, p. 3790, of record) may be cited as an evidentiary reference in the following rejections to teach that the density of liquid iodine pentafluoride (IF5) is 3.2 g/cm3 (g/mL) (see Table IV on p. 3793) and that the molecular weight (MW) of IF5 is 221.9 g/mol (top of Table I on p. 3791).
When converting from a weight of IF5 to mol of IF5, the weight in grams (g) is divided by the molecular weight in (g/mol). For example: X g IF5 x (1 mol/221.9 g IF5) = Y mol IF5.
When converting from a volume of IF5 to mol of IF5, the volume in (mL) is converted to weight in (g) using the density, and then the weight is converted to moles using the MW as shown above. For example, X mL IF5 x (3.2 g/mL IF5) x (1 mol/221.9 g IF5) = Y mol IF5.
The same calculations are applied when other chemicals have to be converted between volume, weight, and moles.
It is also noted that a concentration of mol per liter (mol/L) is equivalent to a concentration recited in mmol per mL (mmol/mL); and that the conversion between mmol to mol and mL to L is 1000 to 1.
Claim Rejections - 35 USC § 102
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action. See p. 4-6 of the OA dated 5/18/2026 regarding rejection of record.
Claim(s) 12-20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Otsuka (JP2018104408A, published on 7/8/2018; US equivalent = US2020/0087230, published on 3/19/2020, both of record) as evidenced by Dichloromethane (“Density” from PubChem record for CID 6344 downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Dichloromethane#section=Density&fullscreen=true on 5/8/2026, of record).
Otsuka teaches an example 2 in [0207] comprising a liquid solution of 6.6 g (20 mmol) of IF5-HF-pyridine complex and 5 mL of dichloromethane (a halogenated hydrocarbon). Otsuka teaches examples 3-5 in [0208-0218] comprising a liquid solution of 3.85 g (12 mmol) of IF5-HF-pyridine complex and 2.5 mL of dichloromethane. Otsuka teaches an example 6 in [0219-0223] comprising a liquid solution of 7.70 g (24 mmol) of IF5-HF-pyridine complex and 10 mL of dichloromethane. These correspond to concentrations of IF5 in dichloromethane of 4 mmol/mL; 4.8 mmol/mL; and 2.4 mmol/mL respectively. Therefore, all of these solutions meet the limitations of claims 11 and 13-20.
Further regarding claim 12, as evidenced by Dichloromethane, the density of said compound is 1.3 g/mL. Therefore, example 2 comprises 6.5 g dichloromethane; examples 3-5 comprise 3.25 g dichloromethane; and example 6 comprises 13 g dichloromethane. The total composition mass (dichloromethane + IF5-HF-pyridine complex) is 13.1 g for example 2; 7.1 g for examples 3-5; and 20.7 g for example 6. The mass percentage of dichloromethane is 50% for example 2; 46% for examples 3-5; and 63% in example 6. Therefore, all of the liquid solutions meet the limitations of claim 12. Also see MPEP 2131.
Response to the Arguments filed on 15-17 of the Response filed on 8/17/2026:
Regarding the rejection over Otsuka, Applicant argues:
“For example, in Example 2, 6.6 g (20 mmol) of the IFs-HF-pyridine complex, 5 mL of dichloromethane, 2.32 g (20 mmol) of ethyl pyruvate, and 0.8 mL (10 mmol) of S2Cl2 were used. However, although ethyl pyruvate is a substrate, it is a liquid at room temperature and can therefore also be considered an organic solvent. Given that the density of ethyl pyruvate is approximately 1.05 g/mL, its volume is approximately 2.21 mL. Consequently, the concentration of IFs is approximately 2.33 mol per liter of organic solvent. The following URL states that ethyl pyruvate is a liquid and lists its density. See https://labchem- wako.fujifilm.com/us/product/detail/W01iWo0105-0529.html. Below is a snippet of the website…
Similarly, in Example 3, IF5 amounts to approximately 3.01 mol per liter of organic solvent; in Example 4, IF5 amounts to approximately 2.46 mol per liter of organic solvent; in Example 5, IF5 amounts to approximately 2.99 mol per liter of organic solvent; and in Example 6, IF5 amounts to approximately 1.96 mol per liter of organic solvent.
As stated above, since the present invention limits the amount of IF5 to 3.5 mol or more per liter of organic solvent, the present invention is neither described nor suggested in Otsuka. Further, Otsuka has no justification for setting the IF5 amount at 3.5 mol or more per liter of organic solvent.
For the reasons set forth above, Otsuka fails to anticipate the amended claims. Accordingly, reconsideration and withdrawal of the rejection are respectfully requested.”
The Applicant’s arguments have been fully considered but are not persuasive. The full text for Example 2 in [0207] recites:
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As indicated in the rejection, the first step in the example is forming “a solution” by adding 20 mmol of an IF5-HF-pyridine complex (thus containing an acid, HF, and a base, pyridine, and IF5 in a 1:1:1 molar ratio-also see [0142]) and then 5 mL of dichloromethane to an autoclave. 20 mmoL/5 mL = 4 mmoL/1 L or 4 mol per liter. This value falls within the claimed value of “in an amount of 3.5 mol or more per liter of the organic solvent”. See MPEP 2131.
The Applicant appears to be arguing the solution after ethyl pyruvate and S2Cl2 are added thereto, however, this was not the solution relied upon the rejection. Therefore, any arguments regarding the mixture of IF5-HF-pyridine complex, dichloromethane, ethyl pyruvate and S2Cl2 is not relevant to the rejection of record. The same argument applies to examples 3-5 of Otsuka, wherein the first step of said examples is to form a solution consisting of the same components as example 2, only in a different concentration of the IF5-HF-pyridine complex (4.8 moles per liter). The amendment is sufficient to distinguish the claimed composition from that of example 6 of Otsuka, wherein the concentration of the IF5-HF-pyridine complex is only 2.4 mol per liter.
Conclusion
THIS ACTION IS MADE FINAL. 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 AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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