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Updated: Apr 18, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Hydrogen-deuterium exchange of aromatic amines and amides using deuterated trifluoroacetic acid
Richard Giles1, Amy Lee1, Erica Jung1
1Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089, USA.
Abstract:
The H-D exchange of aromatic amines and amides, including pharmaceutically relevant compounds such as acetaminophen and diclofenac, was investigated using CF3COOD as both the sole reaction solvent and source of deuterium label. The described method is amenable to efficient deuterium incorporation for a wide variety of substrates possessing both electron-donating and electron-withdrawing substituents. Best results were seen with less basic anilines and highly activated acetanilides, reflecting the likelihood of different mechanistic pathways.
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