Boron tribromide → HCID 59485749, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-3-(4-methoxy-phenyl)-4-(3-trifluoromethyl-phenyl)-oxazolidin-2-one (57 mg, 0.169 mmol, prepared from (S)-4-(3-trifluoromethyl-phenyl)-oxazolidin-2-one and 1-iodo-4-methoxy-benzene using the same condition as example 4) in CH2Cl2 (1 mL) is cooled down to −78° C. in a dry ice bath when BBr3 (0.371 mmol, 1M in CH2Cl2) is added into the mixture dropwise. After the addition, the mixture is allowed to warm up to 0° C. and stirred for 1 h. The reaction is then quenched at 0° C. by adding MeOH (0.5 mL) and diluted with water (2 mL). After extraction with CH2Cl2 (3×2 mL), the combined organic layers were concentrated and purified by a flash column chromatography (silica gel, EtOAc/hexane 0˜50%) to provide the desired (S)-3-(4-hydroxy-phenyl)-4-(3-trifluoromethyl-phenyl)-oxazolidin-2-one (47 mg, 86%). HPLC-MS calculated for C16H12F3NO3 (M+H+) 324.1, found 324.1.

Provenance & Evidence