A Continuous-Flow Approach to 3,3,3-Trifluoromethylpropenes: Bringing Together Grignard Addition, Peterson Elimination, Inline Extraction, and Solvent Switching
- Trevor A. Hamlin†
- Gillian M. L. Lazarus†
- Christopher B. Kelly†
- Nicholas E. Leadbeater*†‡
- †Department of Chemistry, University of Connecticut, United States
- ‡Department of Community Medicine & Health Care, University of Connecticut Health Center, United StatesRead the publication that featured this abstract
A continuous-flow approach to the synthesis of 3,3,3-trifluoromethylpropenes involving Grignard addition of (trimethylsilyl)methylmagnesium chloride to a trifluoromethyl ketone followed by dehydrative desilylation of the α-trifluoromethyl-β-hydroxysilyl alcohol using trimethylsilyl trifluoromethanesulfonate is reported. An inline aqueous/organic extraction and a concomitant solvent switch were key to the success of the methodology. Transition from batch to continuous flow conditions allows for higher yields, shorter reaction times, and facile scale out.
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