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Issue 16, 2000
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Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds in the presence of reusable zeolites

Keith Smith,*a  Gamal A. El-Hiti,a  Mark E. W. Hammond,a  Dawoud Bahzad,a  Zhaoqiang Lia  and  Christophe Siqueta 
Author affiliations

* Corresponding authors

a Centre for Clean Chemistry, Department of Chemistry, University of Wales Swansea, Singleton Park, Swansea, UK

Abstract

Reactions of mono-substituted aromatics of moderate activity with bromine in the presence of stoichiometric amounts of zeolite NaY proceed in high yield and with high selectivity to the corresponding para-bromo products. The zeolites can easily be regenerated by heating and reused. Similar para-selectivity can be achieved in the case of toluene by use of tert-butyl hypobromite as reagent, zeolite HX as catalyst, and a solvent comprising a mixture of tetrachloromethane and diethyl ether. Radical bromination of ethyl 4-methylbenzoate using bromine in the presence of light is catalysed by various zeolites and affords a high yield of ethyl 4-(bromomethyl)benzoate but with no great improvement in selectivity for monobromination.

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Publication details

The article was received on 16 Mar 2000, accepted on 13 Jun 2000 and first published on 19 Jul 2000


Article type: Paper
DOI: 10.1039/B002157L
Citation: J. Chem. Soc., Perkin Trans. 1, 2000,0, 2745-2752
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    Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds in the presence of reusable zeolites

    K. Smith, G. A. El-Hiti, M. E. W. Hammond, D. Bahzad, Z. Li and C. Siquet, J. Chem. Soc., Perkin Trans. 1, 2000, 0, 2745
    DOI: 10.1039/B002157L

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