Azobisisobutyronitrile → 4'-(Bromomethyl)-2-chloro-1,1'-biphenyl

Participants

Reaction Steps

A mixture of 4′-methyl-2-chloro-biphenyl (1.08 g, 5.33 mmol), NBS (1.14 g, 6.40 mmol) and AIBN (175 mg, 1.06 mmol) in CCl4 (37 mL) was heated at reflux for 3 h. The reaction mixture was diluted with CH2Cl2 and the organic solution was washed sequentially with aqueous saturated NaHCO3 (2×), water (1×), and brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (hexanes to 5% EtOAc-hexanes) to afford the title compound (920 mg). 1H NMR (CDCl3 400 MHz) δ 7.63-7.25 (m, 8H), 4.56 (s, 2H).

Provenance & Evidence