Water → 1-(Benzyloxy)-2-bromobenzene

Participants

Reaction Steps

To a mixture of 7.45 g (43.1 mmol, Aldrich) of 2-bromophenol, and 6.9 g (50 mmol) of anhydrous potassium carbonate in 25 mL dimethylformamide (DMF) (Burdick and Jackson) heated to 80° was added dropwise 7.37 g (43.1 mmol, Aldrich) of benzyl bromide over 10 minutes. The reaction mixture was stirred at 80° for 1 hour then cooled to room temperature, added to 100 mL of water and extracted with two 50 mL portions of 1:5 ethyl ether/hexane. The organic extracts were combined, washed with 50 mL of 1M aqueous NaOH solution, 50 mL of water, dried (magnesium sulfate) and concentrated in vacuo to afford 10.6 g (40.3 mmol, 94%) of title compound as a colorless liquid.

Provenance & Evidence