25004-95-9

The invention relates to a trifluoromethylsulfinyl halide (chemical formula of F. 3 Process CSOX) of, This compound is used as a pesticide, for the preparation of pesticides and fine chemicals, in particular for preparing insecticide fipronil, and its preparation process :1) trichloromethyl thionyl chloride, i.e. Cl3 Reaction of CSCl with oxidant gives trichloromethyl sulfinyl chloride, (Cl)3 CSOCl;2) Trichloromethyl sulfinyl chloride Cl3 Reaction of CSOCl) with fluoride to give trifluoromethanesulphonyl halide, i.e. F3 CSOX. Has the advantage: that the preparation of trifluoromethylsulfinyl halide avoids the low boiling, highly toxic starting materials and intermediates, namely trifluoromethyl sulfachloride and di (trifluoromethyl) bisulfide, has the advantages, of simple, efficient, safe; convenience and the like, and uses cheap and readily available raw material trichloromethyl sulfur chloride or a mixture, thereof to reduce manufacturing cost. (by machine translation)

Starting from chlorofluoromethane (3), prepared by a convenient procedure, fluoromethanesulfonyl chloride (6) was synthesized easily and cleanly via the intermediate thioethers 4-chlorobenzyl fluoromethyl sulfide (4) or benzhydryl fluoromethyl sulfide (5) for the first time.Reaction of 6 with trimethylamine leads to an inverse amine-adduct 9a of fluorosulfene, which was characterized by transformation to (fluoromethyl)trimethylammonium chloride (10) and by oxidation to the sulfonate 11.The structure of 9a is discussed on the basis of spectroscopic data.Bromomethanesulfonyl chloride (17) similarly as chloromethanesulfonyl chloride leads to a dimeric adduct 18a of (bromomethylsulfonyl)sulfene and trimethylamine, which is characterized by its hydrolysis product 19a. 2,4-Dibromo-1,3-dithietane 1,1,3,3-tetraoxide (15) could not be detected, but has been prepared by another method.The products, resulting from the monohalogenmethanesulfonyl chlorides, can be explained by the intermediate existence of the monohalogensulfenes.Difluoro- (20) and dichloromethanesulfonyl chloride (24) gave no sulfeneamine adducts; 20 yields (difluoromethyl)trimethylammonium chloride and other products while from 24 under various conditions only trimethylammonium trichloromethanesulfinate (25) is formed.

The reactivity of N-sulfinyl compounds R6NSO 2 in ene-reactions shows a large variation depending on the nature of the group R6.Haloalkanesulfonamide derivatives react even with very unreactive alkenes.The scope of this method for the synthesis of sulfinic acid amides and the side reactions are discussed.