Azobisisobutyronitrile → 1-Azido-4-(bromomethyl)benzene

Participants

Reaction Steps

A mixture of p-azidotoluene (3.9 g), N-bromosuccinimide (5.5 g) and azobisisobutyronitrile (1.0 g) in carbon tetrachloride (30 ml) was heated under reflux in the dark under nitrogen for 18 h. The reaction mixture was allowed to cool to room temperature and the solvent was removed in vacuo. The residue was dissolved in ether (50 ml) and filtered. Evaporation of solvent gave an oil (6.5 g) which was chromatographed on silica gel (200 g, Merck 7734). Elution with petroleum ether (b.p. 40°-60°) gave the title compound as an oil (2.37 g). I.R. (Neat) 2120 cm-1.

Provenance & Evidence