Phosphorus oxybromide → HCID 53429144, compound

Participants

Reaction Conditions

Reaction Steps

(6-(Benzyloxy)pyridin-3-yl)methanol (3 g, 14 mmol) was added to a solution of phosphorus oxybromide (4.8 g, 16.8 mmol) in DCM (40 mL) under N2 at 0° C. The mixture was stirred at 20° C. for 1 hour. The mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc) to afford 2-(benzyloxy)-5-(bromomethyl)pyridine. MS ESI calc'd. for C13H13BrNO [M+H]+ 278 and 280. found 278 and 280. 1H NMR (400 MHz, DMSO-d6) δ 8.27 (d, J=2.4 Hz, 1H), 7.81-7.79 (m, 1H), 7.45-7.31 (m, 5H), 6.90 (d, J=8.4 Hz, 1H), 5.35 (s, 2H), 4.72 (s, 2H).

Provenance & Evidence