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Iodination of stable aromatic diazonium salt using crosslinked poly (4‐vinylpyridine)‐supported iodide
Author(s) -
Karimi Zarchi Mohammad Ali,
Ebrahimi Nahid
Publication year - 2011
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.35297
Subject(s) - chemistry , iodide , aryl , hydrochloric acid , acetonitrile , reagent , amine gas treating , salt (chemistry) , polymer chemistry , sodium nitrite , halogenation , polymer , diazonium compounds , inorganic chemistry , organic chemistry , alkyl
An efficient and simple method for the iodination of stable arenediazonium salts has been developed by using a polymer‐supported iodide. The arenediazonium chlorides, Ar‐N 2 + Cl − , were obtained by the reaction between primary aryl amine and sodium nitrite in the presence of concentrated hydrochloric acid (HCl) at low temperature (0–5°C). By ion exchange reaction between Ar‐N 2 + Cl − with NaBF 4 , the stable arenediazonium tetrafluoroborates, Ar‐N 2 + BF 4 − , were prepared. Ar‐N 2 + BF 4 − , were then converted to aryl iodides by crosslinked poly (4‐vinylpyridine)‐supported iodide, [P 4 ‐VP]I, in acetonitrile at room temperature. The spent polymeric reagent was regenerated and reused for several times without losing its activity. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012