Benzoyl Peroxide → 2-(Bromomethyl)-3-phenylquinoxaline

Participants

Reaction Steps

A mixture of 2-methyl-3-phenylquinoxaline (2.00 g, 9.08 mmol), NBS (1.45 g, 8.17 mmol) and benzoyl peroxide (catalytic amount) in carbon tetrachloride (75 mL) was heated at reflux for 5 h, then allowed to cool to r.t. The reaction mixture was filtered, the filtrate was concentrated in vacuo and the residue purified by column chromatography (SiO2, 0-20% EtOAc in heptane) to give the title compound (1.22 g, 45%) as a cream-coloured solid. δH (CDCl3) 8.11-8.19 (m, 2H), 7.75-7.85 (m, 4H), 7.52-7.62 (m, 3H), 4.76 (s, 2H). LCMS (ES+) 299.1, 301.1 (M+H)+, RT 4.10 minutes (Method 3).

Provenance & Evidence