1-Bromo-2-nitrobenzene → 4'-Methyl-2-nitro-1,1'-biphenyl

Participants

Reaction Steps

A solution of 5.0 g (19.6 mmol) 4-(trimethylstannyl)toluene, 4.08 g (20.2 mmol) 1-bromo-2-nitrobenzene, and 138 mg (0.2 mmol) bis(triphenylphosphine)palladium(II) chloride in 100 mL DMF was heated to 110° C. for 4 hours. The mixture was cooled to room temperature, was poured into a mixture of brine and 1N KOH, then was extracted 3 times with ether. The combined organic material was washed with 1N KOH, was washed with brine, was dried over magnesium sulfate, was stripped of solvent in vacuo, and was chromatographed on silica gel under medium pressure using 5% ethyl acetate in hexanes to give 3.76 g (90% yield) of the title compound as a light lemon-yellow colored oil. Rf 0.31 in 10% EtOAc/hexane, visualized by UV and ammonium molybdate/ceric sulfate stain.

Provenance & Evidence