Benzoyl Peroxide → 6-(Bromomethyl)quinoxaline

Participants

Reaction Steps

To a solution of 6-methylquinoxaline (10.0 g, 69.4 mmol) in CCl4 (80 mL) was added NBS (13.5 g, 76.3 mmol) and benzoyl peroxide (BP, 1.7 g, 6.9 mmol) at room temperature. The mixture was heated at reflux for 2 hours. After cooling, the mixture was evaporated under vacuum to give a yellow solid, which was extracted with Petroleum Ether (50 mL×5). The extracts were concentrated under vacuum. The organics were combined and concentrated to give crude 6-bromomethylquinoxaline (12.0 g), which was used directly in the next step. 1H NMR (300 MHz, CDCl3) δ 8.85-8.87 (m, 2 H), 8.10-8.13 (m, 2 H), 7.82 (dd, J=2.1, 8.7 Hz, 1 H), 4.70 (s, 2 H).

Provenance & Evidence