Benzyl Bromide → 1-(Benzyloxy)-3-fluorobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution containing 2-bromo-5-fluorophenol (50 g, 0.26 mol) in 500 mL acetone was added potassium carbonate (54.2 g, 0.39 mmol) and benzyl bromide (34.3 mL, 0.288 mol). The reaction was heated at reflux under an argon atmosphere for 2 h and then allowed to cool to 25° C. The acetone was removed under reduced pressure and the residue was taken up in ether (400 mL). The organic layer was washed with water (5×100 mL) and brine (1×100 mL) and then dried (MgSO4). The solution was then concentrated under reduced pressure and subjected to flash chromatography using hexane as the eluent. In this manner, 2-benzyloxy-4-fluorobenzene was obtained as a white solid. 1H NMR (300 MHz, CDCl3): δ 5.14 (s, 2 H), 6.57-6.63 (m, 1 H), 6.69 (dd, J=2.7, 10.2 Hz, 1 H), 7.32-7.52 (m, 6 H).

Provenance & Evidence