Water → 2-(4-Methoxyphenyl)benzonitrile

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Reaction Steps

4-methoxyphenylmagnesium bromide (280 g, 15% solution in tetrahydrofuran) is added dropwise over seven hours to a refluxing solution of 2-bromobenzonitrile (32 g), palladium (II) chloride (1.3 g) and triphenylphosphine (3.8 g) in tetrahydrofuran (210 ml). [HPLC: yield 94-95%]. After cooling to room temperature and the addition of water (50 ml), tetrahydrofuran is removed under vacuum. The residue is extracted with toluene (230 ml). Insoluble material is filtered off and the solvent distilled off. The crude product is recrystallised from ethanol to give 4'-methoxybiphenyl-2-carbonitrile as a solid, m.pt. 82-83° C. 1H NMR (CDCl3): 3.90(s,3H), 7.02(d,2H), 7.36-7.52(m,4H), 7.59-7.65(m,1H), 7.74(d,1H).

Provenance & Evidence