Benzyl Bromide → 3-(Benzyloxy)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 3-cyanophenol (20 g) in dry N,N-dimethylformamide (200 mL) is treated with sodium hydride (5.6 g; 60% dispersion in mineral oil), portionwise during 40 minutes, followed by dropwise addition of benzyl bromide (20 mL). The mixture is heated at 90° C. for 4 hours, cooled and concentrated under reduced pressure. The residue is partitioned between ethyl acetate and water and the organic layer washed with 1 N sodium hydroxide (100 mL) followed by drying over magnesium sulphate and concentration. The residue is recrystallised from methanol to give 3-benzyloxybenzonitrile (24 g), in the form of a cream solid, m.p. 38-40° C.

Provenance & Evidence