Triphenylphosphine → (1,1'-Biphenyl)-4-carbonitrile, 4'-methyl-

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Reaction Steps

4-methylphenylmagnesium chloride (98 g, 20% solution in tetrahydrofuran) is added dropwise over five hours to a refluxing solution of 4-bromobenzonitrile (20 g), palladium (II) chloride (0.78 g) and triphenylphosphine (2.3 g) in tetrahydrofuran (100 ml). [HPLC: yield 91-93%]. After cooling to room temperature tetrahydrofuran is removed under vacuum. The residue is taken up in toluene/water (1:1) (200 ml) and filtered. The aqueous phase is separated off. Solvent is removed by distillation and the crude product recrystallised from ethanol to give 4'-methylbiphenyl-4-carbonitrile as a solid, m.pt. 107-109° C. 1H NMR (CDCl3): 2.41(s,3H), 7.29(d,2H), 7.49(d,2H), 7.66 (d,2H), 7.71 (d,2H).

Provenance & Evidence