Iranian chemical communication 2423-4958 7 Issue 4. pp. 230-306, Serial No. 25 2019 10 01 Cyanation and bromination of electron-rich aromatics by BrCN under solvent-free conditions catalyzed by AlCl3: A new examples of Beckmann-type rearrangement 251 263 3925 10.30473/icc.2018.3925 EN Nader Noroozi Pesyan Faculty of Chemistry, Urmia University, 57159, Urmia, Iran Ali Gharib Department of Chemistry, Islamic Azad University, Mashhad, Iran Azam Monfared Department of Chemistry, Tehran Centre branch, Payam-e-Noor University, Tehran, Iran Journal Article 2016 10 06 A convenient route for cyanation and bromination of some electron-rich aromatics (anisole, 1,3-dimethoxybenzene, 1,4-dimethoxybenzene, 1,3,5-trimethoxybenzene and β-naphthol) by BrCN in the presence of aluminum trichloride (AlCl3), as catalyst, by grinding method under solvent-free conditions at room temperature to 60 °C was described in good yield. The structures of all obtained products were characterized by FT-IR, 1H NMR, 13C NMR, and Mass spectrometry techniques. Anisole and 4-cyanobenzonitrile afforded both cyanated and brominated products. 1,3-Dimethoxybenzene yielded to two types of the cyanated products. 1,4-Dimethoxybenzene has done some unusual coupling reactions via new Beckmann-type rearrangement. No bromination of 1,4-dimethoxybenzene was observed under the same conditions. 1,3,5-Trimethoxybenzene and β-naphthol obtained both cyanated and brominated products which were analyzed by HPLC technique. https://icc.journals.pnu.ac.ir/article_3925_6dafb0e79c3f5856c2ff593b6f28d69b.pdf