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Synlett 1999; 1999(9): 1403-1404
DOI: 10.1055/s-1999-2867
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Facile Substitution of N,N-Dimethylanilines and Phenols with Trifluoroacetaldehyde Ethyl Hemiacetal

Yuefa Gong* , Katsuya Kato, Hiroshi Kimoto
  • *National Industrial Research Institute of Nagoya, Hirate-cho, Kita-ku, Nagoya 462-8510, Japan; Fax + 81(52)9 11 24 28
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Publication Date:
31 December 1999 (online)

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2,2,2-Trifluoro-1-(N,N-dimethylaminophenyl)ethanols were easily formed in excellent yields by electrophilic substitution between N-N-dimethylanilines 1a, b and trifluoroacetaldehyde ethyl hemiacetal (TFAE). The corresponding substitution of phenols 2a-e to prepare 2,2,2-trifluoro-1-(hydroxyphenyl)ethanols, however, occurred only in the presence of catalytic amounts of anhydrous potassium carbonate.

α-trifluoromethylbenzylic alcohol - N,N-dimethylaniline - phenol - trifluoroacetaldehyde ethyl hemiacetal - aromatic substitution