Sodium Hydroxide → 2,3-Dimethyl-1H-indol-5-ol

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Reaction Steps

To a solution of 2,3-dimethyl-5-methoxyindole (175 mg, 1 mmol), (J. Chem. Soc. 1957, 3175-3180) in methylene (5 ml) cooled at −60° C. was added boron tribromide (210 μl, 2.2 mmol) dropwise. After completion of addition, the mixture was left to warm up to ambient temperature and was stirred for 1 hour. Water was added and the pH was adjusted to 6 with 2N sodium hydroxide. The mixture was extracted with ethyl acetate and the organic layer was separated, washed with brine, dried (MgSO4) and evaporated to give 2,3-dimethyl-5-hydroxyindole (124 mg, 77%).

Provenance & Evidence