Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam
Publication type: Journal Article
Publication date: 2019-08-22
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
A convenient and efficient three-step synthesis of 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride, the key building block of penoxsulam, is described. The main features of the synthesis include a regioselective lithiation and subsequent electrophilic substitution starting from commercially available 3-bromobenzotrifluoride to provide (2-bromo-6-(trifluoromethyl)phenyl)(propyl)sulfane, then a copper-catalyzed C–O coupling to introduce the difluoroethoxy moiety and chloroxidation conditions to give the desired sulfonyl chloride.
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Zheng Z. J., Xu L. Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam // Synthesis. 2019. Vol. 51. No. 22. pp. 4249-4252.
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Zheng Z. J., Xu L. Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam // Synthesis. 2019. Vol. 51. No. 22. pp. 4249-4252.
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TY - JOUR
DO - 10.1055/s-0039-1690617
UR - https://doi.org/10.1055/s-0039-1690617
TI - Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam
T2 - Synthesis
AU - Zheng, Zhan Jiang
AU - Xu, Li
PY - 2019
DA - 2019/08/22
PB - Georg Thieme Verlag KG
SP - 4249-4252
IS - 22
VL - 51
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2019_Zheng,
author = {Zhan Jiang Zheng and Li Xu},
title = {Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam},
journal = {Synthesis},
year = {2019},
volume = {51},
publisher = {Georg Thieme Verlag KG},
month = {aug},
url = {https://doi.org/10.1055/s-0039-1690617},
number = {22},
pages = {4249--4252},
doi = {10.1055/s-0039-1690617}
}
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MLA
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Zheng, Zhan Jiang, and Li Xu. “Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam.” Synthesis, vol. 51, no. 22, Aug. 2019, pp. 4249-4252. https://doi.org/10.1055/s-0039-1690617.