Benzoyl Peroxide → 2-(Bromomethyl)quinoxaline

Participants

Reaction Steps

2-methylquinoxaline (1 g, 6.9 mmol) was dissolved in CCl4 (15 mL), and then 1-bromopyrrolidine-2,5-dione (1.8 g, 10.4 mmol) and benzoyl benzenecarboperoxoate (1.0 g, 4.2 mmol) were added. The mixture was stirred overnight at reflux. The solids were removed by filtration. The filtrate was washed with brine and dried over sodium sulfate. After evaporation of the solvent, the residue was dissolved in DCM and purified on silica gel using 40% hexane/AcOEt to afford 2-(bromomethyl)quinoxaline (714 mg, 46% yield); 1H NMR (400 MHz, DMSO-d6): δ 4.94 (s, 2H), 7.84-7.90 (m, 2H), 8.04-8.11 (m, 2H), 9.09 (s, 1H).

Provenance & Evidence