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Synthesis of 3,4-dibromo-3,4,4-trichloro-1-phenylbutan-1-one and 1-aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones from 3,4,4-trichlorobut-3-enoic acid

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Abstract

Bromination of 3,4,4-trichlorobut-3-enoic acid in boiling carbon tetrachloride led to the formation of 2-bromo-3,4,4-trichlorobut-3-enoic acid as a result of replacement of hydrogen in the CH2 group. The reaction at 40°C involved the double C=C bond to give 3,4-dibromo-3,4,4-trichlorobutanoic acid. The brominated acids were converted into the corresponding chlorides which were used to acylate benzene, toluene, and bromobenzene according to Friedel-Crafts. The acylation was not selective, and only the reaction of 3,4-dibromo-3,4,4-trichlorobutanoyl chloride with benzene gave 3,4-dibromo-3,4,4-trichloro-1-phenylbutan-1-one as the only product. 1-Aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones were synthesized by bromination of the corresponding 1-aryl-3,4,4-trichlorobut-3-en-1-ones which were prepared previously by Friedel-Crafts acylation of substituted benzenes with 3,4,4-trichlorobut-3-enoyl chloride.

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    V. I. Potkin, S. K. Petkevich, R. V. Kaberdin & P. V. Kurman

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  1. V. I. Potkin
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  2. S. K. Petkevich
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  3. R. V. Kaberdin
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  4. P. V. Kurman
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Correspondence to V. I. Potkin.

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Original Russian Text © V.I. Potkin, S.K. Petkevich, R.V. Kaberdin, P.V. Kurma, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 11, pp. 1621–1625.

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Potkin, V.I., Petkevich, S.K., Kaberdin, R.V. et al. Synthesis of 3,4-dibromo-3,4,4-trichloro-1-phenylbutan-1-one and 1-aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones from 3,4,4-trichlorobut-3-enoic acid. Russ J Org Chem 43, 1617–1621 (2007). https://doi.org/10.1134/S107042800711005X

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  • DOI: https://doi.org/10.1134/S107042800711005X

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