US 7,534,906 B2
Process for the synthesis of hydrogenofluoromethylenesulphonyl radical derivatives
Laurent Saint-Jalmes, Lyons (France)
Assigned to Rhodia Chimie, Aubervilliers (France)
Appl. No. 10/519,287
PCT Filed Jun. 24, 2003, PCT No. PCT/FR03/01940
§ 371(c)(1), (2), (4) Date Nov. 25, 2005,
PCT Pub. No. WO2004/002951, PCT Pub. Date Jan. 08, 2004.
Claims priority of application No. 02/08090 (FR), filed on Jun. 28, 2002.
Prior Publication US 2006/0178536 A1, Aug. 10, 2006
Int. Cl. C07C 309/00 (2006.01); C07C 303/00 (2006.01)
U.S. Cl. 558—44  [562/114] 12 Claims
 
1. A process for the synthesis of compounds having a hydrofluoromethylenesulfonyl radical from an alkyl thiolate, the process comprising the steps of:
a) reacting (1) an alkyl thiolate and an associated cation with (2) a compound exhibiting a carbon of sp3 hybridization carrying a hydrogen, a fluorine, a heavy halogen selected from the group consisting of chlorine, bromine and iodine, and an electron-withdrawing group which is fluorine or a group having a Hammett constant (σp ) value of at least equal to 0.2, in a solvent; and
b) oxidizing the compound formed in step a) in the presence of an aqueous phase;
said solvent of step a) being a water-immiscible solvent, an aqueous phase or a two-phase combination of a water-immiscible solvent and of an aqueous phase, said aqueous phase comprising at most ⅓ by weight of water-miscible nonaqueous solvent; with a ratio of the amount, in equivalents, of the alkyl sulfide to the amount, in moles, of water being at most equal to 50.