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analysis of the crude product using 1,3,5-triisopropylbenzene as an internal
standard. dYield of product was determined by 19F NMR using PhCF3 as an internal
standard.
DOI: 10.1039/D0CC06004F
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To demonstrate the synthetic application of the present
haloflorocyclopropanation, we used TMSCFCl2 to synthesize a
compound A that was used as a hypolipemic agent3 (Scheme
4). Vinyl phenol reacted with ethyl 2-bromo-2-
methylpropionate to give ethyl 2-methyl-2-(4-vinylphenoxy)
propanoate (6a). Intermediate 6a was then treated with
TMSCFCl2 to give A in 70% yield.
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O
O
OH
O
K2CO3
MeCN
Br
O
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+
O
6a
, 58%
Cl
F
O
O
O
O
n-Bu4NBr (5 mol%)
O
CFCl
TMS
+
O
2
toluene, 110 o
C
A
6a
, 70%
Scheme 4 Synthesis of chlorofluorocyclopropane A used as a
hypolipemic agent.
This work was financially supported by the Natural Science
Foundation of China (Nos. 21632009 and 214210025), the Key
Programs of the Chinese Academy of Sciences (No. KGZD-
EWT08), the Key Research Program of Frontier Sciences of CAS
(No. QYZDJ-SSW-SLH049), Shanghai Science and Technology
Program (No. 18JC1410601), the Natural Science Foundation
of Zhejiang Province (Nos. LY18B020003, LY18B020002), and
Chemical Engineering & Technology of Zhejiang Province First-
Class Discipline (Taizhou University).
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Conflicts of interest
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17 X. Liu, C. Xu, M. Wang and Q. Liu, Chem. Rev., 2015, 115, 683.
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Prakash, G. A. Olah, Angew. Chem. Int. Ed. 2011, 50, 7153; (4) L.
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There are no conflicts to declare.
Notes and references
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20
For
the
proposed
reaction
mechanism
of
halofluorocyclopropanation with TMSCFCl2 and TMSCFBr2, see
Scheme S1 and S2 in electronic supplementary information (ESI).
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4 | J. Name., 2012, 00, 1-4
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