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Bromombthylation of aromatic hydrocarbons

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    Bromomethyiation of toluene, ethylbenzene, and cumene gave high yields (about 80%) of the corresponding mono(bromomethyl) derivatives in the form of a mixture of ortho and para isomers, the quantitative proportions of which were. established by the method of oxidation into the corresponding benzenedicarboxylic acids.

  2. 2.

    It was shown that in the chloro- and bromo-methylation of these aromatic hydrocarbons under identical conditions, mixtures of mono(halomethyl) derivatives of the same composition are formed.

  3. 3.

    In the brômomethylation of toluene, ethylbenzene, and cumene the substitutent has a steric effect on orientation in the reaction which is analogous to that observed in the chloromethylation of these hydrocarbons (as we pass from toluene to ethylbenzene and further to cumene, the relative amount of para isomer rises sharply).

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Authors and Affiliations

  1. N. D. Zelinsky Institute of organic Chemistry of the Academy of Sciences of the USSR, USSR

    I. N. Nazarov & A. V. Semenovsky

Authors
  1. I. N. Nazarov
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  2. A. V. Semenovsky
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Nazarov, I.N., Semenovsky, A.V. Bromombthylation of aromatic hydrocarbons. Russ Chem Bull 6, 225–228 (1957). https://doi.org/10.1007/BF01170557

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  • DOI: https://doi.org/10.1007/BF01170557

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