tert-Butylsulfinamide, (S)-(-)- → HCID 89717940, compound

Participants

Reaction Steps

Under an inert atmosphere the light yellow solution of 2,2-difluoro-1-(2-fluorophenyl)ethanone (8.0 g, 45.9 mmol) in THF (280 ml) was treated at r.t. with (S)-2-methylpropane-2-sulfinamide (5.68 g, 45.9 mmol) followed by titanium(IV)ethoxide (21.0 g, 19.3 ml, 91.9 mmol). The light yellow solution was heated to reflux and stirred for 2 hours. The reaction mixture was cooled to r.t., poured into half-saturated brine, diluted with AcOEt (100 ml) and stirred vigorously for 1 hour. After filtration through a layer of Dicalite® and washing with AcOEt the aqueous layer was separated and extracted with AcOEt (2×150 ml). The organic layers were dried over MgSO4 and evaporated at reduced pressure. The crude product was purified by flash chromatography on silica gel (eluent: heptane/AcOEt 10:1) to give (S,Z)—N-(2,2-difluoro-1-(2-fluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide (8.27 g, 64.9% yield) as a yellow oil. MS: m/z=278.0 [M+H]+.

Provenance & Evidence