tert-Butanol → (RS)-4-(5-bromo-2-fluoro-phenyl)-4-methyl-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of the crude (RS)-4-bromo-1-fluoro-2-(2-iodo-1-isocyanato-1-methyl-ethyl)-benzene (10.01 g, 26 mmol) in N,N-dimethyl-formamide (90 ml) was treated at room temperature with silver tetrafluoroborate (5.58 g, 29 mmol) and tert-butanol (3.86 g, 52 mmol). The yellow suspension was stirred at 80° C. overnight. For the workup, the reaction mixture was evaporated at reduced pressure, the residue triturated in ethyl acetate then filtered. The solution was concentrated at reduced pressure and the crude product purified by chromatography on silica gel using a gradient of dichloromethane/methanol=100/0 to 40/60 as the eluent. The (RS)-4-(5-bromo-2-fluoro-phenyl)-4-methyl-oxazolidin-2-one was obtained as a white solid (4.33 g, 61% of theory). MS (ISP): m/z=274.2 [M+H]+, 276.2 [M+2+H]+.

Provenance & Evidence