Ethyl Acetate → 2-methyl-1H-indol-7-ol

Participants

Reaction Steps

To a solution of 2-methyl-7-methoxy indole (814 mg, 5.0 mmol) in CH2Cl2 (20 mL) at 0° C. was added BBr3 (15 mL, 15 mmol, 1M in CH2Cl2), and then the ice bath was removed and stirring was continued for 3 h. Ice was added and the reaction mixture diluted with water (30 mL). The aqueous layer was extracted with EtOAc (3×100 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via passage through a short silica gel column (20% then 50% EtOAc/hex) to afford 2-methyl-7-hydroxy indole as an unstable solid (99% yield).

Provenance & Evidence