Hydrogen Peroxide → 2-Cyano-4'-methylbiphenyl

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Reaction Steps

Equimolar amounts of 2-bromobenzonitrile and 4-methylphenylboronic acid are combined with tetrakis[triphenylphosphine] palladium, toluene, sodium carbonate and ethanol and refluxed vigorously, with stirring for 6 to 12 hours, preferably overnight. The mixture is allowed to cool to 10° to 30° C., preferably ambient temperature and hydrogen peroxide is added. The mixture is stirred, extracted with ether, washed with water, and dried over magnesium sulphate to produce an oil, 4-methyl-2'-cyanobiphenyl, a compound of Formula (35. To this oil, equimolar amounts of N-bromosuccinimide and azaisobutylnitrile are added, in a nonpolar solvent (such as ether, cyclohexane, or carbon tetrachloride; preferably carbon tetrachloride), and the mixture is heated under reflux for 1 to 4 hours, preferably 2 hours. The mixture is cooled and filtered, and the solvent is extracted to yield 4-(bromomethyl)-2'-cyanobiphenyl.

Provenance & Evidence