Benzyl Bromide → 3-(benzyloxy)-5-bromopyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4.4 g (23.2 mmol) 5-bromo-3-hydroxy-1H-pyridin-2-one and 1.2 g (30 mmol) NaOH in 116 mL MeOH was added benzyl bromide dropwise at room temperature. The resulting mixture was heated to 60° C. overnight. After cooling, the volatiles were removed in vacuo, 20 mL water and 40 mL EtOAc were added, and the aqueous phase was extracted 2× with 20 mL EtOAc. The combined organics were dried over Na2SO4 and evaporated. Purification by automated flash chromatography (80 g silica gel cartridge 0-100% EtAOc/hex over 30 min) afforded 2.51 g (38.7%) 3-benzyloxy-5-bromo-1H-pyridin-2-one. LCMS [M+H]+=280.1

Provenance & Evidence