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Bromination of 1,3,5-trimethyl-4-chloropyrazole

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The bromination of 1,3,5-trimethyl-4-chloropyrazole with N-bromosuccinimide (NBS) in the presence of benzoyl peroxide leads to 5-bromomethyl-1,3-dimethyl-4-chloropyrazole, whereas 3,5-bis(bromomethyl)-1-methyl-4-chloropyrazole predominates in the case of a twofold excess of NBS. Products of subsequent substitution in the 3- and 5-bromomethyl groups of the 3,5-bis(bromomethyl) compound in a ratio of 3∶1 were detected in small amounts; this is evidently associated with the syn orientation of the bromine atom in the 5-bromomethyl group, which hinders attack by the bromine radical.

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Authors and Affiliations

  1. D. I. Mendeleev Moscow Institute of Chemical Technology, 125820, Moscow

    V. P. Perevalov, A. K. Kh. Karim, A. V. Khrapov, L. I. Baryshnenkova & B. I. Stepanov

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  1. V. P. Perevalov
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  2. A. K. Kh. Karim
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  3. A. V. Khrapov
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  4. L. I. Baryshnenkova
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  5. B. I. Stepanov
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 40–42, January, 1988.

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Perevalov, V.P., Karim, A.K.K., Khrapov, A.V. et al. Bromination of 1,3,5-trimethyl-4-chloropyrazole. Chem Heterocycl Compd 24, 33–36 (1988). https://doi.org/10.1007/BF00475561

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  • DOI: https://doi.org/10.1007/BF00475561

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