ChemInform Abstract: Practical One‐Pot Transformation of Electron‐Rich Aromatics into Aromatic Nitriles with Molecular Iodine and aq NH3 Using Vilsmeier—Haack Reaction.

Abstract

Abstract Various electron-rich aromatics could be efficiently transformed into the corresponding aromatic nitriles in good to moderate yields by treatment with DMF and POCl 3 , followed by the reaction with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH) in aq NH 3 . Some of less reactive aromatics, such as anisole, 1,2-dimethoxybenzene, 1,4-dimethoxybenzene, and mesityrene, could be also transformed into the corresponding aromatic nitriles in good to moderate yields using N -methylformanilide and O(POCl 2 ) 2 , followed by the reaction with molecular iodine in aq NH 3 . Moreover, propiophenone derivatives could be successfully transformed into the corresponding β-chlorocinnamonitriles by the reaction with DMF and POCl 3 , followed by the reaction with molecular iodine and aq NH 3 . These reactions are novel metal-free one-pot methods for the preparation of aromatic nitriles from electron-rich aromatics and β-chlorocinnamonitriles from propiophenones.