1-Bromo-4-fluorobenzene → (S)-N-((S)-(4-bromophenyl)(4-fluorophenyl)methyl)-2-methylpropane-2 sulfinamide

Participants

Reaction Conditions

Reaction Steps

The solution of 1-bromo-4-fluorobenzene (66.7 g, 0.38 mol) in THF (400 mL) was cooled to −78° C. Then n-BuLi (140 mL, 0.38 mol) was dropwise added at −78° C. and maintained at this temperature for about 1 h. (S,E)-N-(4-bromobenzylidene)-2-methylpropane-2-sulfinamide, 19-a, (70 g, 0.19 mol) in anhydrous THF (100 ml) was also dropwise added at −78° C. The mixture was stirred at −78° C. for 1 h, warmed to rt for 2 h, and then quenched by NH4Cl aq. The organic phase was dried and purified by column chromatography (PE:EA=10:1) afford the product 19-b as a light yellow solid, recrystallized by PE:EA=20:1 to give the white solid, (26 g, 35%).

Provenance & Evidence