Azobisisobutyronitrile → 1-Bromo-3-(bromomethyl)-5-methylbenzene

Participants

Reaction Steps

A solution of 1-bromo-3,5-dimethyl-benzene (1.0 g, 5.4 mmol, 1.0 eq), NBS (1.06 g, 5.94 mmol, 1.1 mmol) and AIBN (180 mg, 1.08 mmol, 0.2 eq) in CCl4 (20 mL) was stirred at reflux overnight. The reaction was then diluted with water and extracted with CH2Cl2. The organic extracts were combined and washed with aqueous NaHCO3, dried (Na2SO4), filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (Petroleum ether:EtOAc, 1:0 to 10:1) to give the title compound as a light yellow oil (1.2 g, 84%).

Provenance & Evidence