General procedure for the synthesis of 3-(4-bromophenyl)propanenitrile from diethyl cyanomethylphosphonate and p-bromobenzaldehyde: (2) Prop-2-enenenitrile E/Z mixture of 3-(4-bromophenyl)pyridine (34.8 g, 0.63 L) was dissolved in methanol (0.21 L), and sodium borohydride (8.2 g) was slowly added at 0 °C under nitrogen protection. The reaction mixture was stirred at 100 °C for 1 hour. After completion of the reaction, the reaction solution was concentrated, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated saline, dried over anhydrous magnesium sulfate, filtered and the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent ratio: hexane:ethyl acetate=100:0→65:35) to give the yellow oily product 3-(4-bromophenyl)propionitrile (28.1 g).
