Selective aromatic chlorination and bromination with N-halogeno amines in acidic solution

Francesco Minisci; Eelena Vismara; Francesca Fontana; Eduardo Platone; Giovanni Faraci

doi:10.1039/P29890000123

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Journal of the Chemical Society, Perkin Transactions 2

Issue 2, 1989

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Selective aromatic chlorination and bromination with N-halogeno amines in acidic solution

Francesco Minisci , Eelena Vismara , Francesca Fontana , Eduardo Platone and Giovanni Faraci

J. Chem. Soc., Perkin Trans. 2, 1989, 123-126

DOI: 10.1039/P29890000123

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1,2-Dimethoxybenzene and 3,4-dimethoxytoluene are efficiently chlorinated by N-chlorodialkylamines in sulphuric acid. The reaction has a very marked selectivity for monochlorination of the para-position. The chlorination and bromination of monoalkylbenzenes (toluene, ethyl-, and isopropylbenzenes) under the same conditions is much less selective, but the para/ortho ratio can be reversed going from unsubstituted alkyl groups in the N-halogeno amines to alkyl groups substituted at the β-position by electron-withdrawing groups [morpholine, piperazine, bis(cyanoethyl)amine]. m-Xylene is chlorinated with high selectivity at the 4-position. The nature of the chlorinating species is discussed.

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Francesco Minisci
Eelena Vismara
Francesca Fontana
Eduardo Platone
Giovanni Faraci

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Journal of the Chemical Society, Perkin Transactions 2

Selective aromatic chlorination and bromination with N-halogeno amines in acidic solution

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