Journal of Polymer Research

, 21:330 | Cite as

Diazotization-bromination of aromatic amines using polymer-supported bromide via Sandmeyer-type reaction

Original Paper


A simple, efficient, and mild method for diazotization-bromination of arylamines using poly(4-vinylpyridine)-supported ethyl bromide is reported. Various aromatic amines, with electron-withdrawing groups as well as electron-donating groups, were transformed into aryl diazonium salts in good yields. On the other hand cross-linked poly (4-vinylpyridine) supported ethyl bromide, [P4-VP]Et-Br, was easily prepared and then was applied for synthesis of arylbromide. When [P4-VP]Et-Br in the presence of copper bromide treated with arenediazonium tetrafluoroborate by nucleophilic displacement of Br- by N2 and the nitrogen gas (N2) was evolved. The arylbromide products were characterized by Fourier transform infrared (FT-IR), and some of them were also characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy, and the physical properties were compared to the literature values of known compounds. The advantages of the present method over conventional classical methods are rapid and very simple work-up. The spent polymeric reagents can also be regenerated for several cycles with a little loss of its activity.


Bromination Arylamine Regioselectivity Polymeric reagent Arylbromide 


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Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Mohammad Ali Karimi Zarchi
    • 1
  • S. Zahra Mousavi
    • 1
  1. 1.Department of Chemistry, College of ScienceYazd UniversityYazdIran

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