Journal
SYNTHESIS-STUTTGART
Volume 51, Issue 22, Pages 4249-4252Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690617
Keywords
penoxsulam; regioselective lithiation; benzyne intermediate; C-O coupling; chloroxidation
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Funding
- Natural Science Foundation of Zhejiang Province [LY17E030003]
- Hangzhou Science and Technology Bureau of China [20160432B08, 20170533B08]
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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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