Benzyl Alcohol → 3-(Benzyloxy)-5-bromopyridine

Participants

Reaction Conditions

Reaction Steps

NaH (60% in mineral oil) (40.9 g, 1.03 mol) in 800 mL of DMF was cooled to 0° C. and benzyl alcohol (105 mL, 1.02 mol) was added slowly. The reaction mixture was stirred for 1 h at 20° C., then 3,5-dibromopyridine (200.4 g, 846 mmol) was added and the mixture was stirred for 16 h. The mixture was quenched with saturated NH4Cl (500 mL), diluted with 400 mL of water and extracted with Et2O (5×300 mL). The combined Et2O extracts were washed with 50% brine (6×300 mL) and dried (MgSO4). The solvent was evaporated in vacuo and the crude product was recrystallized from Et2O to afford 161 g (72%) of the title product: mp 63-68° C.; 1H NMR (CDCl3, 300 MHz) δ 5.1 (s, 1H), 7.35-7.50 (m, 6H), 8.27-8.37 (m, 2H); MS (CI/NH3) m/z 264, 266 (M+H)+.

Provenance & Evidence