Triphenylphosphine → [1,1'-Biphenyl]-4-carbonitrile, 4'-(octyloxy)-

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Reaction Steps

4-octyloxyphenylmagnesium bromide (124 g, 25% solution in tetrahydrofuran) is added dropwise over ten hours to a refluxing solution of 4-bromobenzonitrile (17 g), palladium (II) chloride (0.68 g) and triphenylphosphine (2.0 g) in tetrahydrofuran (100 ml). [HPLC: yield 92-94%]. After cooling to room temperature tetrahydrofuran is removed under vacuum. Water (20 ml) and toluene (150 ml) are added and the mixture filtered hot (80-85 C.). The aqueous phase is separated off, and the solvent removed by distillation. The crude product is recrystallised from ethanol/n-hexane to give 4'-octyloxybiphenyl-4-carbonitrile as a solid. 1H NMR (CDCl3): 0.89(t,3H), 1.29-1.50(m,10H), 1.81(quint.2H), 4.00(t,2H), 6.99(d,2H), 7.52(d,2H), 7.63(d,2H), 7.68(d,2H).

Provenance & Evidence