Bis(4-cyanophenyl)methanol

623-00-7

105-07-7

134521-16-7

General procedure for the synthesis of bis(4-cyanophenyl)methanol from 4-bromobenzonitrile and 4-cyanobenzaldehyde: A THF solution (4 ml) of 4-bromobenzonitrile (1.4 g, 7.6 mmol) was slowly added dropwise to a THF solution (10.5 ml) of 1.3 M of the 1PrMgCl LiCl complex at -15 °C, the dropwise addition process continued for 15 min. The resulting brown solution was stirred at -15°C for 30 minutes, followed by continued stirring at the same temperature for 1.5 hours. Subsequently, the solution was slowly added dropwise to a THF solution (4 ml) of 4-cyanobenzaldehyde (1.0 g, 7.6 mmol) at -15°C and the dropwise process was continued for 10 minutes. The reaction mixture was stirred at 0°C for 1 h and then the reaction was quenched with saturated aqueous NH4Cl solution (20 ml). Extraction was carried out by adding TBME (30 ml) and water (20 ml). After separation of the organic layer, the aqueous phase was further extracted with TBME (2 x 20 ml). The organic layers were combined, washed with saturated aqueous NaCl, dried over anhydrous Na2SO4 and concentrated under reduced pressure. To the crude product (2 g) was added EtOAc/heptane (1:2) mixed solvent. The insoluble light yellow solid (0.54 g) was collected by filtration, dissolved in diethyl ether and precipitated with pentane to give a light yellow solid product 10u (0.49 g, 27.5% yield). The mother liquor was concentrated under reduced pressure and purified by rapid chromatography on silica gel (eluent: EtOAc/heptane, 1:2) to give an additional light yellow solid product 10u (0.23 g, 13% yield).