Sodium Hydroxide → 5-Bromo-3-methyl-1H-indole

Participants

Reaction Steps

To a solution of 5-bromo-1H-indole-3-carbaldehyde (5.0 g, 22.3 mmol) in THF (80 mL) was added LiAlH4 (1.70 g, 44.6 mmol). The resulting solution was stirred for 2 h under reflux, then poured into 1N NaOH solution (150 mL), extracted with ethyl acetate (3×100 mL), dried over anhydrous sodium sulfate, and then concentrated under vacuum to give a residue, which was purified via silica gel chromatography (3% ethyl acetate in petroleum ether) to afford 5-bromo-3-methyl-1H-indole as a white solid (3.4 g, 73%).

Provenance & Evidence