Boron tribromide → 5-Hydroxy-2-methyl-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

5-methoxy-2-methyl-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester (0.32 g, 1.4 mmol) was dissolved in dichloromethane (10 mL) and cooled to 0° C. A solution of boron tribromide in dichloromethane (1.0 M, 3.5 mL, 3.5 mmol) was added. After 1 hr at 0° C., the reaction was diluted with dichloromethane and washed with brine. The organic phase was dried and concentrated. The residue was dissolved in 7:1 benzene:methanol (10 mL) and treated with TMSCHN2 (1.0 M in hexane) until gas evolution ceased. Removal of the solvent gave a residue which was chromatographed on silica gel eluting with 7:3 hexane:ethyl acetate to give the title compound.

Provenance & Evidence