Benzoyl Peroxide → 5-Bromo-2-(bromomethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-methyl-pyridine (3.00 g, 17.4 mmol) was dissolved in Carbon tetrachloride (40.0 mL) and N-Bromosuccinimide (3.41 g, 19.2 mmol) was added. Benzoyl peroxide (0.23 g, 0.95 mmol) was added and the mixture was heated at 80° C. overnight. The reaction was cooled to room temperature and filtered to remove the succinimide. The filtrate was concentrated under reduced pressure. Purification by silica gel chromatography using 10% EtOAc/hex as the eluting solvent to obtain 5-bromo-2-bromomethyl-pyridine as a lachrymatory lilac oil (1.34 g, 31%). LCMS (m/e) 251 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.63 (d, 1H, J=2.2 Hz), 7.81 (dd, 1H, J=2.2 and 8.3 Hz), 7.34 (d, 1H, J=8.3 Hz), 4.50 (s, 2H).

Provenance & Evidence