N-bromobutanimide → 2-(4-(Bromomethyl)phenyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(p-tolyl) pyridine (118.88 g, 702.5 mmol), N-bromosuccinimide (131.29 g, 737.6 mmol, 1.05 equivalents) and CCl4 (1190 mL) was treated with benzoyl peroxide (1.70 g, 7.03 mmol, 0.01 equivalents) under nitrogen, stirred at 70° C. for 1.5 hours, and then allowed to cool to ambient temperature with stirring overnight. The reaction mixture was filtered, washed with CCl4 (2×250 mL), concentrated to oil, treated with isopropyl alcohol (420 mL) and cooled to −5° C. The resulting solid was filtered, washed with isopropyl alcohol (140 mL), and dried in a vacuum oven with a N2 bleed to afford the title compound (111.91 g, 64.2% yield). 1H NMR (CDCl3): δ 8.70(m, 1H), 7.99(m, 2H), 7.75(m, 2H), 7.52(m, 2H), 7.25(m, 1H), 4.58 (s, 2H).

Provenance & Evidence