期刊
JOURNAL OF POLYMER RESEARCH
卷 21, 期 1, 页码 -出版社
SPRINGER
DOI: 10.1007/s10965-013-0330-2
关键词
Bromination; Arylamine; Regioselectivity; Polymeric reagent; Arylbromide
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, [P-4-VP]Et-Br, was easily prepared and then was applied for synthesis of arylbromide. When [P-4-VP]Et-Br in the presence of copper bromide treated with arenediazonium tetrafluoroborate by nucleophilic displacement of Br- by N-2 and the nitrogen gas (N-2) 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 (H-1 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.
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