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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
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).Further Information
Publication History
Received: 31 May 2019
Accepted after revision: 06 August 2019
Publication Date:
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
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