1,2,3-Trimethoxybenzene → 1-Bromo-2,3,4-trimethoxybenzene

Participants

Reaction Steps

Pyrogallol trimethyl ether (5.1 g) was suspended in CCl4 (60 mL) and N-bromosuccinimide (6.5 g, 1.2 eq.) was added. The reaction mixture was heated at reflux for 20 hours. The succinimide was collected and the filtrate concentrated in vacuo to a brown oil. The oil was separated by gravity column chromatography (hexane-ethyl acetate, 19: 1) and yielded the title compound as a yellow oil (5.9 g, 78%): EIMS m/z 234 ((M+ —CH3, 81Br), 232 (M+ —CH3, 79Br), 107, 95, 69, 58, 44; 1H NMR (CDCl3, 300 MHZ) δ 7.21 (1H, d, J=9.0 Hz, H6), 6.58 (1H, d, J=9.0 Hz, H5), 3.91 (3H, s, OCH3), 3.89 (3H, s, OCH3), 3.85 (3H, s, OCH3).

Provenance & Evidence