Practical one-pot transformation of electron-rich aromatics into aromatic nitriles with molecular iodine and aq NH 3 using Vilsmeier–Haack reaction

S Ushijima, K Moriyama, H Togo

Index: Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2012 , vol. 68, # 24 p. 4588 - 4595

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Citation Number: 20

Abstract

Various electron-rich aromatics could be efficiently transformed into the corresponding aromatic nitriles in good to moderate yields by treatment with DMF and POCl3, followed by the reaction with molecular iodine or 1, 3-diiodo-5, 5-dimethylhydantoin (DIH) in aq NH3. Some of less reactive aromatics, such as anisole, 1, 2-dimethoxybenzene, 1, 4- dimethoxybenzene, and mesityrene, could be also transformed into the corresponding ...