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Reaction of 4-Substituted 1-[(Difluoromethyl)sulfinyl]-2,3,4,5-tetrafluorobenzenes with Ammonia and Methylamine

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Abstract

The reaction of 4-X-substituted 1-[(difluoromethyl)sulfinyl]-2,3,5,6-tetrafluorobenzenes (X = CF3, H, OMe) with methylamine and ammonia in MeCN, Et2O, and hydrocarbons occurs involves nucleophilic substitution in position 2 of the substrate. The reaction time increases with increasing donor ability of substituent X in the series X = CF3 < H < OMe, as well as with decreasing solvent polarity. Further substitution of fluorine in position 6 of the substrate by methylamine is also possible, but requires a higher reaction temperature. The reaction of ammonia with 1-[(difluoromethyl)sulfinyl]-4-methoxy-2,3,5,6-tetrafluorobenzene is accompanied by partial demethylation to form 2-[(difluoromethyl)sulfinyl]-3,4,6-trifluoro-5-methoxy-N-methylaniline and 4-[(difluoromethyl)sulfinyl]-2,3,5,6-tetrafluorophenol.

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ACKNOWLEDGMENTS

Analytical and spectral measurements were performed at the Chemical Research Center for Collective Use, Siberian Branch, Russian Academy of Sciences.

Funding

The work was performed in framework of the State order to the Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    B. V. Koshcheev, A. M. Maksimov, V. E. Platonov & R. A. Bredikhin

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  1. B. V. Koshcheev
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  2. A. M. Maksimov
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  3. V. E. Platonov
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  4. R. A. Bredikhin
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Correspondence to A. M. Maksimov.

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Koshcheev, B.V., Maksimov, A.M., Platonov, V.E. et al. Reaction of 4-Substituted 1-[(Difluoromethyl)sulfinyl]-2,3,4,5-tetrafluorobenzenes with Ammonia and Methylamine. Russ J Org Chem 56, 1911–1919 (2020). https://doi.org/10.1134/S1070428020110044

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