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. 2022 Nov 21:18:1567-1574.
doi: 10.3762/bjoc.18.167. eCollection 2022.

Simple synthesis of multi-halogenated alkenes from 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane)

Yukiko Karuo  1 , Atsushi Tarui  1 , Kazuyuki Sato  1 , Kentaro Kawai  1 , Masaaki Omote  1
Affiliations

Simple synthesis of multi-halogenated alkenes from 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane)

Yukiko Karuo et al. Beilstein J Org Chem. .

Abstract

A series of aryl fluoroalkenyl ethers that contain chlorine and bromine as well as fluorine atoms were prepared in moderate to good yields via the reactions of phenols and 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane) in the presence of KOH. This simple reaction enabled the construction of highly halogenated compounds with the potential for further functionalization. The reaction involved a highly reactive difluoroethylene intermediate, which was produced by the reaction between halothane and KOH.

Keywords: aryl 1-monofluorovinyl ether; electrophilic 1,1-difluoroethene; halothane; multi-halogenated alkene; phenol.

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Figures

Figure 1
Figure 1
Medicines containing a difluoromethylene group.
Scheme 1
Scheme 1
Reaction of phenol with polyfluoroalkanes.
Figure 2
Figure 2
Fluoroalkene analogs of some drugs.
Scheme 2
Scheme 2
Proposed mechanism.
Scheme 3
Scheme 3
Sonogashira cross-coupling reaction of 2a with trimethylsilylacetylene.
See this image and copyright information in PMC

References

    1. Terrell R C, Speers L, Szur A J, Treadwell J, Ucciardi T R. J Med Chem. 1971;14:517–519. doi: 10.1021/jm00288a014. - DOI - PubMed
    1. Dmowski W. J Fluorine Chem. 2011;132:504–511. doi: 10.1016/j.jfluchem.2011.05.024. - DOI
    1. Guo Y, Shreeve J M. J Fluorine Chem. 2007;128:1280–1285. doi: 10.1016/j.jfluchem.2007.06.004. - DOI
    1. Sasada Y, Shimada T, Ushioda M, Matsui S. Liq Cryst. 2007;34:569–576. doi: 10.1080/02678290701284279. - DOI
    1. Itoh T, Kanbara M, Ohashi M, Hayase S, Kawatsura M, Kato T, Miyazawa K, Takagi Y, Uno H. J Fluorine Chem. 2007;128:1112–1120. doi: 10.1016/j.jfluchem.2007.05.004. - DOI

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