N-bromobutanimide → 3-Bromo-2,6-dimethoxytoluene

Participants

Reaction Steps

A solution of 1,3-dimethoxy-2-methylbenzene (1.86 g, 12.2 mmol) and N-bromo-succinimide (2.17 g, 12.2 mmol) in acetonitrile (30 mL) was stirred at 60° C. for 20 h. After most of the solvent was removed in vacuo, extraction in ethyl ether (2×75 mL) with water (2×50 mL) and flash chromatography with silica gel (gradient to 5% ether/hexanes) provided the title compound as a colorless liquid (2.51 g, 89% yield): 1H NMR (300 MHz, CDCl3) δ 2.19 (s, 3H), 3.78 (s, 3H), 3.81 (s, 3H), 6.54 (d, 1H, J=8.8 Hz), 7.32 (d, 1H, J=8.8 Hz).

Provenance & Evidence