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Bromination of 1-(4-nitrophenyl)-2-formylpyrrole

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Depending on the amount of bromine, the bromination of 1-(4-nitrophenyl)-2-formylpyrrole with bromine in chloroform without a catalyst gives 5-bromo and 4,5-dibromo derivatives. 4-Bromo-1-(4-nitrophenyl)-2-formylpyrrole is formed in the presence of excess AlC13, while a mixture of 3,4- and 4,5-dibromo derivatives with preponderance of the latter is formed with excess bromine. The results are compared with the literature data on the bromination of 2-formylpyrrole, 2-formylfuran, and 2-formylthiophene and are interpreted with allowance for the electronacceptor effect of the p-nitrophenyl substituent attached to the nitrogen atom of the pyrrole ring.

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Authors and Affiliations

  1. Krasnodar Polytechnic Institute, 350006, Krasnodar

    É. Baum, L. I. Belen'kii, V. G. Kul'nevich & T. E. Goldovskaya

  2. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, 117913, Moscow

    É. Baum, L. I. Belen'kii, V. G. Kul'nevich & T. E. Goldovskaya

Authors
  1. É. Baum
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  2. L. I. Belen'kii
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  3. V. G. Kul'nevich
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  4. T. E. Goldovskaya
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 662–665, May, 1982.

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Baum, É., Belen'kii, L.I., Kul'nevich, V.G. et al. Bromination of 1-(4-nitrophenyl)-2-formylpyrrole. Chem Heterocycl Compd 18, 499–502 (1982). https://doi.org/10.1007/BF00526086

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  • DOI: https://doi.org/10.1007/BF00526086

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