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

Participants

Reaction Steps

A mixture of 3-bromophenol (10.0 g, 57.8 mmol) and 325 mesh potassium carbonate (8.79 g, 63.6 mmol) in DMF (100 mL) is treated dropwise with benzyl bromide (9.89 g, 57.8 mmol) and then stirred for 20 hours at room temperature under N2. The reaction is filtered, and the filtrate is acidified with 1 N HCl. The mixture is then diluted with water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 10/1 hexanes/ethyl acetate to afford about 14.55 g (96%) of the titled compound. Rf=0.86 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3).

Provenance & Evidence