Dichloromethane → methyl 6-hydroxy-1H-indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a dichloromethane (10 mL) solution of 6-methoxy-1H-indole-2-carboxylic acid methyl ester (500 mg, 2.44 mmol) was added boron tribromide (12.2 mL, 12.2 mmol) at −78° C., which was stirred for 50 minutes at 0° C. under nitrogen atmosphere. To the reaction solution was added water at 0° C. followed by extraction with ethyl acetate. The organic layer was washed with sat. NaCl followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (395 mg, 85%) as a white solid.

Provenance & Evidence