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Synthesis 1995; 1995(11): 1353-1354
DOI: 10.1055/s-1995-4116
short paper
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A Novel Non-Acidic Method for the Preparation of 2,2,2-Trifluoro-1-(3-nitrophenyl)ethanone and 1-Nitro-3-trifluoromethylbenzene, Versatile Starting Materials for Trifluoromethyl-Containing Aromatic Compounds

Hitomi Suzuki* , Atsuo Tatsumi, Hideo Suzuki, Koichi Maeda
  • *Department of Chemistry, Faculty of Science, Kyoto University, Sakyo-ku, Kyoto 606-01, Japan, Fax +81(75)7512085
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Publication Date:
31 December 2000 (online)

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Treatment of 2,2,2-trifluoro-1-phenylethanone (1) and α,α,α-trifluorotoluene (3) with ozone or ozonized air in chlorinated hydrocarbons in the presence of excess nitrogen dioxide and a catalytic amount of iron(III) salt at -10-0°C leads to the respective title nitro compounds 2 and 4 in good to excellent yields. The reaction is clean and rapid, little or no hydrolysis of the trifluoromethyl group being observed during the nitration.

aromatic nitration - nitrogen dioxide - ozone - trifluoromethyl-bearing arenes