N-bromobutanimide → 3-Bromo-5-(bromomethyl)-2-fluoropyridine

Participants

Reaction Steps

N-Bromosuccinimide (4.732 g, 26.59 mmol) and benzoyl peroxide (0.1356 g, 0.5598 mmol) were added to a solution of 3-bromo-2-fluoro-5-methylpyridine (Matrix Innovation Inc., Montreal, Quebec, Canada 5.318 g, 27.99 mmol) in CCl4 (50 mL), and the mixture was heated at gentle reflux under a N2 atmosphere for 16 h. The mixture was filtered, washing with CCl4, and the residue concentrated and purified by flash chromatography on silica (1% to 1.5% EtOAc/hexane) to give 3-bromo-5-(bromomethyl)-2-fluoropyridine (1.593 g, 21.17% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H); 8.03 (dd, J=8.02, 2.15 Hz, 1H); 4.43 (s, 2H); 19F NMR (376 MHz, CDCl3) δ −65.17 (br. s., 1F). Sample did not ionize well in ESI+ mode.

Provenance & Evidence