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Synthesis 2019; 51(22): 4249-4252
DOI: 10.1055/s-0039-1690617
DOI: 10.1055/s-0039-1690617
paper
Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam
Autor*innen
This work was supported by the Natural Science Foundation of Zhejiang Province (LY17E030003) and the Hangzhou Science and Technology Bureau of China (20160432B08 and 20170533B08).
Weitere Informationen
Publikationsverlauf
Received: 31. Mai 2019
Accepted after revision: 06. August 2019
Publikationsdatum:
22. August 2019 (online)
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.
Key words
penoxsulam - regioselective lithiation - benzyne intermediate - C–O coupling - chloroxidationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690617.
- Supporting Information (PDF) (opens in new window)
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