Thionyl bromide → 4-(Bromomethyl)-2-methylpyridine

Participants

Reaction Steps

To a solution of (2-methylpyridin-4-yl)-methanol (0.510 g, 4.14 mmol) in 8 mL of dichloromethane was added thionyl bromide (1.03 g, 4.97 mmol) dropwise. After 1 h, the reaction was quenched with saturated aqueous ammonium chloride. The organic solution was washed 2× with water, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 4-(bromomethyl)-2-methylpyridine that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 188.0 (81Br) for [M+H]+.

Provenance & Evidence