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Updated: Feb 23, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Detrifluoroacetylative Generation of Halogenated Enolates: Practical Access to Perhalogenated Ketones and Alkenes
Kaluvu Balaraman1, Max Moskowitz1, Yang Liu1
1Georgetown University, Chemistry Department, Washington, DC, USA.
Abstract:
Sequential chlorination/fluorination of aromatic trifluoroacetylated ketones gives 1-aryl 2-chloro-2,4,4,4-tetrafluoro-butan-1,3-dione hydrates that are used for the synthesis of ketones and alkenes exhibiting a terminal bromochlorofluoromethyl group. The hydrates undergo detrifluoroacetylative cleavage and subsequent bromination in the presence of a copper(II)bisoxazoline catalyst, K2CO3 and NBS at room temperature. The corresponding bromochlorofluoromethyl ketones can be applied in Wittig and Horner-Wadsworth-Emmons reactions and dibromoalkenylations.
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