N-bromobutanimide → 5-(Bromomethyl)-2-fluoropyridine

Participants

Reaction Steps

A mixture of 2-fluoro-5-methyl-pyridine (15.00 mL, 135 mmol), N-bromosuccinimide (24.03 g, 135 mmol) and benzoyl peroxide (1.635 g, 6.75 mmol) in carbon tetrachloride (100 mL) was heated at reflux for 2.5 h. The mixture was cooled and filtered through a medium-fritted funnel. The solid was rinsed with DCM (3×50 ml). The filtrate was concentrated to give 5-(bromomethyl)-2-fluoropyridine (25.7 g, 135 mmol, 100% yield) as an orange oil. m/z (ESI, +ve ion) 191.9 (M+H)+. The mixture was immediately carried into the next step of the synthesis without further purification.

Provenance & Evidence