4,4'-Dibromobiphenyl → HCID 86762389, compound

Participants

Reaction Steps

Toluene (250 mL) was bubbled with nitrogen for 15 min, followed by addition of triphenylphosphine (0.2 g, 0.8 mmol) and Pd(OAc)2 (0.05 g, 0.2 mmol). The mixture was bubbled with nitrogen for 15 min, then N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (3.4 g, 10.5 mmol), 4,4′-dibromobiphenyl (6.6 g, 21.0 mmol), sodium tert-butoxide (2.0 g, 21.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 12 h. After cooling, the reaction mixture was filtered through a silica pad and washed with toluene. The solvent was removed in vacuo and the residue was purified by flash chromatography using 20% toluene/hexane to afford N-([1,1′-biphenyl]-4-yl)-N-(4′-bromo-[1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (4.2 g, 73% yield) as a white solid.

Provenance & Evidence