Methanol → Methyl 5-bromopyridine-3-carboxylate

Participants

Reaction Steps

A solution of 5-bromonicotinic acid (10 g, 49.5 mmol) in MeOH (200 mL) was cooled to 0° C. and conc. H2SO4 (5 mL) was added dropwise. The reaction mixture was heated to reflux for 12 h. After completion, the reaction mixture was concentrated under reduced pressure, diluted with water and the aqueous layer was washed with EtOAc. The resulting mixture was poured over an aqueous saturated NaHCO3 solution to adjust the pH 7-8, it was then extracted with EtOAc and the organic layer was dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure to get the solid product methyl 5-bromonicotinate as an off-white solid (7 g, yield 66%): 1H NMR (400 MHz, CDCl3) δ 9.14 (s, 1H), 8.86 (s, 1H), 8.45 (s, 1H), 3.98 (s, 3H)

Provenance & Evidence