Hydrogen Bromide → 4-(bromomethyl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

Hydrobromic acid (2 mL) was added to a solution of 4-(hydroxymethyl)pyridin-2(1H)-one (200 mg, 1.6 mmol) was at 0° C. The mixture was stirred at 110° C. for 3 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/MeOH) to afford the 4-(bromomethyl)pyridin-2(1H)-one. MS ESI calc'd. for C6H7BrNO [M+H]+ 188 and 190. found 188 and 190. 1H NMR (400 MHz, DMSO-d6) δ 11.55 (s, 1H), 7.36 (d, J=6.8 Hz, 1H), 6.39 (s, 1H), 6.17 (d, J=6.8 Hz, 1H), 4.45 (s, 2H).

Provenance & Evidence