Chloroform → 3-Bromo-6-methoxy-2-methylpyridine

A mixture of 5-bromo-6-methyl-1H-pyridin-2-one (5.5 g, 29 mmol), silver carbonate (10.89 g, 39 mmol), iodomethane (13.6 mL, 217 mmol) and chloroform (115 mL) is stirred overnight in the dark at room temperature. Triethylamine (10 mL) is added and stirring continued for 1.5 hr. The reaction mixture is filtered through a pad of Hi-Flo and the filtrate is washed with water (100 mL), dried, filtered and concentrated. The residue is purified by filtration through a pad of silica gel washing with cyclohexane-20% ethyl acetate. The solvent is concentrated to afford 3-bromo-6-methoxy-2-methylpyridine (3.7 g, 63% yield) as an oil. LC/MS RT 3.76 min; MS m/e=202/204 (M); NMR (CDCl3) 7.6 (1H, d), 6.43 (1H, d), 3.89 (3H, s), 2.57 (3H, s).