反应详情

4-methylphenylmagnesium chloride (49 g, 20% solution in tetrahydrofuran) is added dropwise over eight hours to a refluxing solution of 3-bromobenzonitrile (10 g), palladium (II) acetate (2.4 g) and triphenylphosphine (5.8 g) in tetrahydrofuran (200 ml). [HPLC: yield 89-91%]. After cooling to room temperature tetrahydrofuran is removed under vacuum. The residue is taken up in toluene/water (3:1) (200 ml ) and the aqueous phase separated off. The solvent is removed by distillation and the crude product purified by column chromatrography (Kieselgel 60; n-hezane/acetone 3:1) to give 4'-methylbiphenyl-3-carbonitrile as a solid, m.pt. 59-61° C. 1H NMR (CDCl3): 2.41(s,3H), 7.29(d,2H), 7.46(d,2H), 7.49-7.63(m,2H) 7.77-7.85(m,2H).

1. customis removed under vacuum
2. customthe aqueous phase separated off
3. customThe solvent is removed by distillation
4. customthe crude product purified by column chromatrography (Kieselgel 60; n-hezane/acetone 3:1)