Diethyl Ether → Dimethyl-thiocarbamic acid S-(4-bromo-2-hydroxymethyl-6-nitro-phenyl)ester

Participants

Reaction Steps

5-Bromo-2-dimethylcarbamoylsulfanyl-3-nitro-benzoic acid ethyl ester (3.0 g, 9.4 mmol) is taken up in THF (40 mL)/diethyl ether (10 mL) and cooled to zero with an ice bath. Borane in THF (1M, 20 mL, 2.1 mmol) is added dropwise to the reaction and then the reaction warmed to room temperature. An additional equivalent of borane is added, and the reaction warmed to 45° C. The reaction is stirred at 45° C. for 4 hours and then the reaction cooled to zero and quenched by the slow addition of saturated NH4Cl. The reaction is poured into water and then extracted with ethyl acetate. The combined organic layers were dried filtered and evaporated. The residue is purified on silica gel with DCM/MeOH as the eluent to afford 2.5 g (91%) of the title product. LCMS (ESMS): m/z 336.9 (M+H+).

Provenance & Evidence