Dimethyl Sulfate → 4-Bromo-2-chloro-6-methylanisole

Participants

Reaction Steps

4-Bromo-2-chloro-6-methylphenol (50 g, 0.225 mole) and K2CO3 (31.8 g, 0.23 mole) were combined in acetone (300 ml). Dimethyl sulfate (32 ml, 0.34 mole) was added dropwise and the mixture stirred 22 hours at room temperature, filtered and concentrated to an oil in vacuo. The oil was taken up in 250 ml ether, washed 2×2N NaOH, 1× saturated NaHCO3, 2× brine, dried over MgSO4, reconcentrated to an oil and distilled to yield purified title product, 42.9 g, b.p. 122°-124°/0.9 mm, pnmr/CDCl3 /delta/TMS:2.3 (s, 3H), 3.8 (s, 3H), 7.3 (q, 2H).

Provenance & Evidence