Benzyl Bromide → 4'-(Benzyloxy)[1,1'-biphenyl]-4-carbonitrile

Participants

Reaction Steps

In a 250-ml, three-necked, roundbottom flask equipped with a magnetic stirrer, heating mantle, thermometer, and condenser were placed 1.76 g (9.0 mmol) 4-hydroxy-4'-biphenylcarbonitrile, 3.94 g (28.5 mmol) powdered anhydrous potassium carbonate, 1.18 ml (9.92 mmol) α-bromotoluene, and 150 ml acetonitrile. After stirring the mixture under reflux for two hours, TLC analysis showed that none of the phenolic starting material remained. Two-thirds of the acetonitrile was then distilled off, and 200 ml dichloromethane was added. The mixture was filtered through Celite and the solids were washed thoroughly with dichloromethane. Evaporation of the filtrate yielded white crystals which were purified by recrystallization from methanol. 2.17 g (84.4%) of product was obtained; mp 150°-151.5° C. The following structure was confirmed by infrared, nuclear magnetic resonance, and mass spectral analyses. ##STR24##

Provenance & Evidence