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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

Smith, Keith, El-Hiti, Gamal A., Hammond, Mark E. W., Bahzad, Dawoud, Li, Zhaoqiang and Siquet, Christophe 2000. Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds in the presence of reusable zeolites. Perkin 1 (16) , pp. 2745-2752. 10.1039/B002157L

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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.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1472-7781
Last Modified: 04 Jun 2017 02:51
URI: http://orca-mwe.cf.ac.uk/id/eprint/12701

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