Methanol → 3-Bromo-5-methoxy-4-methylpyridine

Participants

Reaction Conditions

Reaction Steps

To a freshly prepared sodium methoxide from sodium metal (0.165 g, 0.0072 mol) and methanol (2.5 mL), 3,5-dibromo-4-methyl-pyridine (1.0 g, 0.0040 mol) dissolved in N,N-dimethylformamide (10 mL) was added and heated at 80° C. overnight. Reaction was diluted with ethyl acetate and quenched with ice water, and layers were separated. The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 8.33 (s, 1H), 8.09 (s, 1H), 3.05 (s, 3H), 2.32 (s, 3H).

Provenance & Evidence