A new access to 3-halo-3,3-difluoropropanoic acid derivatives via fluorine-halogen exchange reaction of silyl enolates of 3,3,3-trifluoropropanoic acid derivatives

Chemistry Letters

Volumn 36, Issue 5, 2007, Pages 636-637

  Shimada, Taichi ^a   Konno, Tsutomu ^a   Ishihara, Takashi ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

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EID: 34250163177     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.636     Document Type: Article

References (23)

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17. Many examples for the halogen-exchange reactions are reported. For instance, see: Chemistry of Organic Fluorine Compounds II. A Critical Review, ed. by M. Hudlicky, A. E. Pavlath, American Chemical Society, Washington, DC, 1995;
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20. The experimental procedure is given in Supporting Information, which is available electronically on the CSJ-Journal Web site, http://www.csj.jp/ journals/chem-lett/index.html.
21. The silyl enolates of 3,3,3-trifluoropropanoic esters, thioester, and amide were confirmed to be prepared under the same reaction conditions as employed for the imide enolates 1.
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23. 4 (2.0 equiv.) at -20°C for 2 h, followed by hydrolysis, gave 5a in 60% yield.