Synthesis of 2-cyano-4’-methylbiphenyl
|School||Hefei University of Technology|
|Keywords||2-cyano-4’-methyl-biphenyl coupling reaction synthesis p-chlorotoluene o-chlorobenzonitrile|
2-cyano-4’-methylbiphenyl, which is a key intermediate used for the preparation of antihypertensive drugs, was synthesized by the couple of p-methyl phenylmagnesium chloride with o-chlorobenzonitrile.In the reaction of p-metheylphenylmagnesium chloride, several factors including the species of materials, solvent were discussed through single-factor approach and the optimum reaction condition was obtained. GC yield of 77.7% p-tolylmagnesiumchloride intermediate in toluene-tetrahydrofuran mixed solvents was obtained based on internal standard analysis.2-cyano-4’-methylbiphenyl was easily synthesized by the coupling of non-active o-chlorobenzonitrile with p-methylphenylmagnesium chloride in toluene-tetrahydrofuran mixed solvents over transition-metal catalysts（MnCl2、CoCl2、NiCl2、CuCl2、Ni（PPh3）2Cl2、CdCl2）. Various reaction conditions, especially catalysis of some catalysts were discussed to improve selectivity suitable for industrialization in the recycle solvent system. The structures of target products-biphenyl compounds were characterized through 1HNMR and IR. In the coupling reaction, various reaction conditions, especially catalysis of some metal catalysts, were discussed to improve product yield and purity to meet commercial use.