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

Participants

Reaction Steps

Benzoyl peroxide (1.570 g, 6.48 mmol) and NBS (23.19 g, 130 mmol) was added to a stirred solution of 2-fluoro-5-methylpyridine (SynQuest Labs, Inc., Alachua, Fla., 14.4045 g, 130 mmol) in CCl4 (125 mL) and the suspension was heated at reflux for 2 h. After cooling, the solution was filtered to remove solid and concentrated, and the residue was purified by flash column chromatography (ISCO Combiflash system, Teledyne ISCO, Lincoln, Nebr., hexanes to 10% ethyl acetate in hexanes) to give 5-(bromomethyl)-2-fluoropyridine (15.11 g, 80 mmol, 61.3% yield) as a yellow solid. LCMS (API-ES) m/z 191 (M+H)+.

Provenance & Evidence