Sodium borohydride → (5-Bromopyridin-2-yl)methanol

Participants

Reaction Steps

A mixture of 5-bromo-pyridine-2-carbaldehyde (0.5 g, 2.68 mmol) in ethanol (30 mL) was cooled in an ice bath. Sodium borohydride (0.41 g, 10.75 mmol) was added and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated, dried, the residue dissolved in dichloromethane (30 mL) and quenched with a saturated aqueous sodium bicarbonate solution. The organic phase was separated and the aqueous phase was extracted further with dichloromethane (2×10 mL). The combined organic phase was dried over sodium sulfate and concentrated to give the product as an off-white solid (426 mg, 84%). 1H NMR (300 MHz, CDCl3): δ (ppm) 8.61 (d, 1H), 7.82 (dd, 1H), 7.23 (d, 1H), 4.73 (s, 2H), 3.92 (bs, 1H).

Provenance & Evidence