Methyl iodide → 3,5-Dibromo-4-methylpyridine

Participants

Reaction Steps

A solution of dry diisopropylamine (11.0 g, 108 mmol) in dry THF under nitrogen was cooled with a −78° C. bath, and n-butyl lithium (2.50 M in hexane, 39 mL) was added. The reactant solution was warmed to ambient temperature, and then cooled to −78° C. again. A solution of 3,5-dibromopyridine (22 g, 93 mmol) in dry THF was added. After stirring at −78° C. for 30 min, CH3I (17 g, 120 mmol) was added, the mixture was warmed to ambient temperature and stirred over night. The reaction was quenched with water, extracted with EtOAc, the organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated. The residue was purified by column chromatography to afford 3,5-dibromo-4-methylpyridine: 1H-NMR (400 MHz, CDCl3) ppm 8.55 (s, 2H), 2.55 (s, 3H);

Provenance & Evidence