Sodium Iodide → 1-(Benzyloxy)-2-bromobenzene

Participants

Reaction Steps

A mixture of 2-bromophenol (1.50 g; 8.67 mmol), benzyl bromide (1.48 mg; 8.65 mmol). potassium carbonate (1.44 g; 10.41 mmol) and sodium iodide (catalytic amount) in 50 mL of acetonitrile was refluxed for 24 hours. After cooling, the solids were filtered off and the filtrate was concentrated. The crude residue was purified on a silica gel column (10% ethyl acetate hexane) to obtain 2.30 g (quantitative yield) of 2-benzyloxybromo- benzene, 1H NMR (CDCl3): δ 5.16 (s, 2H); 6.84 (t, 1H, J=7.6); 6.93 (d, 1H, J=8.3); 7.21-7.49(m, 6H); 7.56 (d, 1H, J=7.8).

Provenance & Evidence