Methyl iodide → 4-Bromo-1-methylpyridin-2(1H)-one

Participants

Reaction Steps

To a solution of 4-bromo-2-hydroxypyridine (0.10 g, 0.57 mmol) in THF (5.0 mL) was added, portion wise, NaH (60% dispersion in mineral oil, 0.02 g, 0.86 mmol). The resulting solution was stirred at room temperature for 5 min followed by addition of methyl iodide (0.11 mL, 1.72 mmol). The reaction mixture was then allowed to stir overnight at room temperature. After the completion of reaction, THF was distilled off, added water and extracted with ethyl acetate (3×25 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated to obtain the desired product (0.10 g, 92%). 1H NMR (DMSO-d6, 400 MHz): δ 3.43 (s, 3H), 6.45 (dd, J=2.40 and 7.20 Hz, 1H), 6.69 (d, J=2.40 Hz, 1H) and 7.68 (d, J=7.20 Hz, 1H). MS: 188.05 (M+H+).

Provenance & Evidence