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

Participants

Reaction Steps

To a cooled (0° C.) solution of 3-bromo-2-chloro-6-methylpyridine (300 mg, 1.45 mmol) in tetrahydrofuran (20 mL), add sodium methoxide (1.57 g, 29 mmol), slowly with stirring. Allow the mixture to warm to ambient temperature and stir overnight. Add additional sodium methoxide (500 mg) and stir at 100° C. overnight. Quench with water (20 mL), extract three times with ethyl acetate (30 mL). Combine the organics and wash with water then brine, and dry over sodium sulphate. Filter and concentrate to give the title product as a yellow solid (135 mg, 46%). 1HNMR (MeOH-d4): δ 7.72 (d, 1H), 6.70 (d, 1H), 3.93 (s, 3H), 2.38 (s, 3H).

Provenance & Evidence