Ethyl 5-bromopyridine-3-carboxylate → (5-Bromo-3-pyridinyl)methanol

Participants

Reaction Steps

To a cold (0° C.) solution of ethyl-5-bromonicotinate (1.0 g, 4.3 mmoL) in MeOH (15 mL) was added sodium borohydride (650 mg, 17 mmol) portion wise. After 30 min. the reaction was quenched by the addition of water (10 mL). The reaction was then extracted with methylene chloride (3×). The extracts were combined, dried (MgSO4) the filtrate was concentrated and purified by column chromatography on silica gel (0 to 80% ethyl acetate/hexanes) to produce 475 mg (60%) as a clear oil. 1H-NMR (CDCl3, 400 MHz) δ 8.57 (s, 1H), 8.49 (s, 1H), 7.91 (s, 1H), 4.73 (s, 2H), 2.51 (s, br, 1H). Mass spec.: 188.12 (MH)+.

Provenance & Evidence