TY - JOUR ID - 3925 TI - Cyanation and bromination of electron-rich aromatics by BrCN under solvent-free conditions catalyzed by AlCl3: A new examples of Beckmann-type rearrangement JO - Iranian chemical communication JA - ICC LA - en SN - 2423-4958 AU - Noroozi Pesyan, Nader AU - Gharib, Ali AU - Monfared, Azam AD - Faculty of Chemistry, Urmia University, 57159, Urmia, Iran AD - Department of Chemistry, Islamic Azad University, Mashhad, Iran AD - Department of Chemistry, Tehran Centre branch, Payam-e-Noor University, Tehran, Iran Y1 - 2019 PY - 2019 VL - 7 IS - Issue 4. pp. 230-306, Serial No. 25 SP - 251 EP - 263 KW - BrCN KW - Electron-rich aromatic compounds KW - Aluminum trichloride KW - solvent-free KW - Intramolecular hydrogen bond KW - Beckmann-type rearrangement DO - 10.30473/icc.2018.3925 N2 - 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. UR - https://icc.journals.pnu.ac.ir/article_3925.html L1 - https://icc.journals.pnu.ac.ir/article_3925_6dafb0e79c3f5856c2ff593b6f28d69b.pdf ER -