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Synthesis of fluorinated halonitrobenzenes and halonitrophenols using tetrafluoroethylene and buta-1,3-dienes as starting building blocks

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Abstract

The gas-phase copyrolysis of tetrafluoroethylene with buta-1,3-diene in a flow reactor at 495–505 °C produces 3,3,4,4-tetrafluorocyclohex-1-ene, which selectively converted to 1,2-difluorobenzene or 1-chloro-2,3-difluorobenzene. The latter can be converted to 2-chloro-3,4-difluoronitrobenzene, 2,3,4-trifluoronitrobenzene, 2,3-difluoro-6-nitrophenol, or 2-chloro-3-fluoro-4-nitrophenol via nitration, fluorodechlorination, and hydrolysis reactions.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    N. V. Volchkov, M. B. Lipkind & O. M. Nefedov

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  1. N. V. Volchkov
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Correspondence to N. V. Volchkov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2156–2163, November, 2021.

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Volchkov, N.V., Lipkind, M.B. & Nefedov, O.M. Synthesis of fluorinated halonitrobenzenes and halonitrophenols using tetrafluoroethylene and buta-1,3-dienes as starting building blocks. Russ Chem Bull 70, 2156–2163 (2021). https://doi.org/10.1007/s11172-021-3327-8

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