N-bromobutanimide → 1,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-

Participants

Reaction Steps

A solution/suspension of 3.74 g (17.5 mmol) 2-nitro-4'-methylbiphenyl, 123 mg (0.9 mmol) AIBN, and 3.43 g (19.3 mmol) NBS in 180 mL CCl4 was refluxed for 30 minutes. The mixture was cooled to room temperature, was filtered through a medium fritted funnel, was washed with water, was dried over magnesium sulfate, was stripped of solvent in vacuo, and was chromatographed on silica gel under medium pressure using 7% ethyl acetate in hexanes to give 4.71 g (92% yield) of the title compound as a light yellow crystalline solid. Rf 0.21 in 10% EtOAc/hexane, visualized by UV and ammonium molybdate/ceric sulfate stain. 1H-NMR (400 MHz, CDCl3): δ7.88 (m, 1H), 7.63 (m, 2H), 7.52 (m, 1H), 7.45 (m, 2H), 7.31 (m, 2H), 4.54 (s, 2H); a small singlet at d 6.69 (benzylic proton) is observed for for the dibrominated material.

Provenance & Evidence