Sodium Azide → 4-(Azidomethyl)benzonitrile

Participants

Reaction Steps

Sodium azide (Aldrich, 3.5 g, 54 mmol) was added to a solution of p-cyanobenzyl bromide (Aldrich, 10 g, 51 mmol) in DMF (100 ml), and the resulting mixture was stirred at ambient temperature for 5 hours. The reaction mixture was then diluted with water (350 ml) and extracted with ether (2×100 ml). Combined organic layers were washed with brine and dried (MgSO4). Removal of solvent gave the title compound (8 g, 96%). 1H NMR (CDCl3): δ 4.42 (s, 2H), 7.41 (d, 2H, J=8.1 Hz), 7.65 (d, 2H, J=8.1 Hz).

Provenance & Evidence