Boron tribromide → 2-(4-Hydroxy-phenyl)-benzo[b]thiophene-6-carboxylic Acid Methyl Ester

Participants

Reaction Steps

To a solution of 2-(4-methoxy-phenyl)-benzo[b]thiophene-6-carboxylic acid methyl ester (500 mg, 1.7 mmol) in dichloromethane (15 mL) at 0° C. is added BBr3 (4.2 mL, 1 M in dichloromethane). The reaction mixture is stirred at ambient temperature overnight. The reaction is quenched by the addition of methanol and concentrated under reduced pressure. The residue is partitioned between EtOAc and 1 N HCl. The organic layer is concentrated and the residue is purified via chromatography eluting with 0 to 25% EtOAc in hexanes to give the title compound (57 mg, 12%) as a tan solid. LC-ES/MS m/e 283 (M−1).

Provenance & Evidence