3,5-Dibromopyridine → 3-Bromo-5-methoxypyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-dibromopyridine (10.0 g, 42.2 mmol) in DMF (10 mL) in a flask with a distillation head was added NaOMe solution 25% wt/wt (10 mL) and the mixture was heated to 100° C. for 3 hours. At the end of 3 hours ˜8 mL of MeOH was collected. The DMF solution was cooled to room temperature and diluted with H2O (25 mL) and extracted with MTBE (2×25 mL). The combined organic layers were washed with H2O (2×25 mL), dried over Na2SO4, filtered and concentrated. The residue was then dried under high vacuum for 10 hours to give the title compound (5.2 g, 66%). 1H NMR (400 MHz, DMSO-D6) δ 8.26-8.31 (m, 2H) 7.69-7.72 (m, 1H) 3.84 (s, 3H).

Provenance & Evidence