N-bromobutanimide → 2-Azido-1-(bromomethyl)-4-iodobenzene

Participants

Reaction Steps

A mixture of the azide from step 1 (9.1 g, 0.035M), N-Bromosuccinimide (6.8 g, 0.039M) and 1,1azobis(cyclohexanecarbonitrile) (0.85 g, 3.5 mmol) in benzene (40 ml) was heated at reflux overnight. The solvent was evaporated under vacuum and the residue was diluted EtOAc (100 ml) and washed with water (50 ml) and brine, dried (MgSO4) and concentrated under vacuum. The residue was purified by chromatography (silica, hexanes) to give the azide as a white solid (8 g, 67%). 1H NMR (500 MHz, CDCl3): δ 4.30 (2H, s), 6.98 (1H, d, J 8.0), 7.35 (2H, t, J 7.0).

Provenance & Evidence