2,3,6-Trimethylphenol → 4-bromo-2,3,6-trimethyl-phenol

Participants

Reaction Steps

To a solution of 2,3,6-trimethylphenol (40 g; 0.294 mol) in DCM (600 ml) at ambient temperature was added a solution of bromine (16.6 ml; 0.294 mol) in DCM (300 ml) dropwise over 30 mins. Reaction stirred for a further 5 hrs at ambient temperature. A solution of 1M sodium sulfite (300 ml) was added. The layers were separated and the aq. layer extracted with DCM (150 ml). Organics combined, washed with half sat. brine (300 ml), dried (anh. MgSO4), filtered and the solvent evaporated to give a white solid (66.2 g; 105% Th.). 1H NMR (300 MHz, CDCl3), δ/ppm; 2.19 (3H, s, Ar—CH3), 2.22 (3H, s, Ar—CH3), 2.34 (3H, s, Ar—CH3), 7.18 (1H, s, Ar—H).

Provenance & Evidence