6-bromo-1H-indole-2-carboxylic acid → (6-Bromo-1H-indol-2-yl)methanol

Participants

Reaction Steps

To a solution of 6-bromo-1H-indole-2-carboxylic acid (1.00 g, 4.20 mmol) in THF (20.0 mL) was added LiAlH4 (1.0 M in THF, 4.20 mL, 4.20 mmol) dropwise at 0° C. The reaction mixture was stirred for 4 h while warming to room temperature. The reaction was quenched with water and 15% aqueous NaOH at 0° C. to form a precipitate which was filtered through Celite. The filtrate was extracted with EtOAc (3×). The extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (696 mg, 73%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 7.51 (s, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.20 (dd, J=8.0, 1.6 Hz, 1H), 6.38 (s, 1H), 4.83 (d, J=5.6 Hz, 2H).

Provenance & Evidence