Methanol → Methyl 5-bromopyridine-3-carboxylate

Participants

Reaction Steps

To a suspension of 5-bromonicotinic acid (20 g, 99.0 mmol) in anhydrous MeOH (100 mL), was carefully added conc. H2SO4 (12 mL) via a syringe. After the addition the reaction mixture was heated to reflux overnight, then cooled to room temperature and concentrated on rotary evaporator. Ice-water (200 mL) was added and a white solid crashed out. The solid was collected by filtration, dissolved in EtOAc (300 mL), washed with aq. NaHCO3, water and brine, dried over MgSO4, filtered and evaporated to give 18 g of 5-Bromo-nicotinic acid methyl ester as a white powder. Yield 84%. 1H NMR (400 MHz, DMSO): 3.88 (s, 3H); 0.74 (s, 3H), 8.43 (s, 1H,), 8.96 (s, 1H), 9.02 (s, 1H). MS (M+H, 217).

Provenance & Evidence