(Cyanomethyl)triphenylphosphonium chloride

• Condenation reactions
• Wittig reactions
• Synthesis of phosphonium-iodonium ylides
• Preparation of α,β-unsaturated esters, amides, and nitriles

107-14-2

603-35-0

4336-70-3

The general procedure for the synthesis of cyanomethyltriphenylphosphonium chloride from chloroacetonitrile and triphenylphosphine was as follows: chloroacetonitrile (10 g, 0.132 mol) was added slowly and dropwise to a toluene solution (120 mL) of triphenylphosphine (23.5 g, 0.0895 mol), and the mixture was subsequently heated to reflux for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the solid product was collected by filtration and washed with ether (2 x 20 mL). The final cyanomethyltriphenylphosphonium chloride (15 g, 49.58% yield) was obtained as a white solid. The product was characterized by NMR hydrogen spectroscopy (400 MHz, DMSO): δ 8.02-7.97 (m, 3H), 7.90-7.79 (m, 12H), 5.94 (s, 1H), 5.90 (s, 1H); Liquid Chromatography-Mass Spectrometry (electrospray ionization, m/z): [M + H]+ = 301.7.