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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.
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