[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Cl)=[CH:4][CH:3]=1.Br[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.[Pd](Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[CH:4][CH:3]=14-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).
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