Polymer-Supported Reagents and 1H–19F NMR Couplings: The Synthesis of 2-Fluoroacetophenone

We describe an experiment for the undergraduate organic laboratory curriculum in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-act...

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Bibliographic Details
Published inJournal of chemical education Vol. 85; no. 6; p. 834
Main Authors Pohl, Nicola, Schwarz, Kimberly
Format Journal Article
LanguageEnglish
Published Easton Division of Chemical Education 01.06.2008
American Chemical Society
Subjects
Chemical synthesis
Couplings
Fluorine
Libraries
NMR
Nuclear magnetic resonance
Organic chemistry
Polymerization
Reagents
Resins
Science education
Spectrum analysis
Second-Year Undergraduate
Hands-On Learning / Manipulatives
Laboratory Instruction
Aldehydes / Ketones
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Summary:We describe an experiment for the undergraduate organic laboratory curriculum in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than 1H without the requirement of a special NMR probe, and to the unique uses of fluorine in molecular design.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed085p834