1-fluoro-1, 1-bis-(phenylsulfonyl)methane and production...

Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfur containing

Reexamination Certificate

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C568S034000

Reexamination Certificate

active

07638654

ABSTRACT:
A novel 1-fluoro-1,1-bis(arylsulfonyl)methane is provided which is useful in monofluoromethylation. Also provided is a production method thereof.A method for producing a fluorobis(arylsulfonyl)methane, the method including the steps of: treating a bis(arylsulfonyl)methane represented by the following formula (1),in-line-formulae description="In-line Formulae" end="lead"?(ArSO2)2CH2  (1)in-line-formulae description="In-line Formulae" end="tail"?(wherein Ar represents a substituted or unsubstituted phenyl group or naphthyl group)with a base; and then adding a fluorination reagent thereto, to produce fluorobis(arylsulfonyl)methane represented by the following formula (2)in-line-formulae description="In-line Formulae" end="lead"?(ArSO2)2CHF  (2)in-line-formulae description="In-line Formulae" end="tail"?(wherein Ar is defined as above), anda fluorobis(arylsulfonyl)methane (2) represented by the above formula (2), which is a novel compound that is very useful in producing a monofluoromethyl.

REFERENCES:
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patent: 2003/0153778 (2003-08-01), Prakash et al.
patent: 2005-511665 (2005-04-01), None
patent: 03/048033 (2003-06-01), None
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Hadjiarapoglou et al. Phenyliodonium Bis(phenylsulfonyl) methylide: A New Hypervalent lodonium Ylide. Journal of the American Chemical Society, 1985, vol. 107, p. 7178 to 7179.
Makoszka et al. Vicarious Nucleophilic Substitution of Hydrogen in Nitrophenyl Toluenesulfonates. Tetrahedron, vol. 53 (13),pp. 4739 to 4750.
Ni et al. Nucleophilic Fluoroalkylation of Epoxides with Fluorinted Sulfones. Journal of Organic Chemistry, 2006, vol. 71, pp. 6829 to 6833.
Fukuzumi et al. Fluorobis(phenylsulfonyl) methane: A Fluoromethide Equivalent and Palladium-Catalyzed Enantioselective Allylic Monofluoromethylation. Angnew. Chemie. Int. Ed. 2006, vol. 45, pp. 4973 to 4977.
International Search Report dated May 22, 2007 in the International (PCT) Application PCT/JP2007/053997 of which the present application is the U.S. National Stage.
Mieczyslaw Makosza et al., “Vicarious Nucleophilic Substitution of Hydrogen in Nitrophenyl Toluenesulfonates”, Tetrahedron, vol. 53, No. 13, pp. 4739-4750, 1997.

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