Benzyl Bromide → 2-(Benzyloxy)-5-bromo-1,3-dimethylbenzene

Participants

Reaction Steps

Dissolve 4-bromo-2,6-dimethyl-phenol (20.1 g, 100 mmol) in DMF (250 mL) under nitrogen. Add cesium carbonate (48.9 g, 150 mmol) and benzyl bromide (13.1 mL, 110 mmol) and heat at 70° C. stirring mechanically for 6 h. Dilute with water (400 mL) and extract with 3/1 diethyl ether/hexanes (2×400 mL). Wash combined organics with brine (300 mL) and then dry (MgSO4), filter and concentrate in vacuo to give 28.67 g (99%) of the title compound as an oil which solidified on standing. 1H NMR(CDCl3): δ7.51-7.37 (m, 5H), 7.22 (s, 2H), 4.82 (s, 2H), 2.31 (s, 6H).

Provenance & Evidence