[F:1][CH:2]([F:12])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([F:11])[CH:4]=1.[CH3:13][C:14]([S@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>ClCCCl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][CH:2]([F:12])[C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[N:19]/[S@@:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])=[C:5]([F:11])[CH:4]=1To a mixture of 4-(difluoromethyl)-2-fluorobenzaldehyde (162 mg, 0.930 mmol) and (R)-2-methylpropane-2-sulfinamide (124 mg, 1.023 mmol) in DCE (3 mL) was added copper sulfate (223 mg, 1.396 mmol). Reaction mixture was heated in a preheated oil bath to 55° C. for 38 hours. The mixture was allowed to cool to room temperature, filtered through a pad of celites and washed with DCE. Combined filtrates were concentrated under reduced pressure to afford (R,E)-N-(4-(difluoromethyl)-2-fluorobenzylidene)-2-methylpropane-2-sulfinamide (266 mg) as a yellow oil, which was used without further purification. LCMS m/z 278.1 (M+H)+, Rt 0.98 min.
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