Benzyl Bromide → 4-(Benzyloxy)-3-hydroxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

3,4-Dihydroxybenzonitrile (5.20 g, 38.5 mmol) and potassium carbonate (5.85 g, 42.4 mmol) were suspended in N,N-dimethylformamide (120 ml), benzyl bromide (4.58 ml) was added, and the mixture was stirred at 50° C. for 3 hours. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate. The mixture was washed with 1N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate 8:1-4:1) to give the title compound.

Provenance & Evidence