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Derivatization of Carboxylic Acids by Reaction With 4'-bromophenacyl Trifluoromethanesulfonate Prior to Determination by High-Performance Liquid Chromatography

Derivatization of Carboxylic Acids by Reaction With 4'-bromophenacyl Trifluoromethanesulfonate Prior to Determination by High-Performance Liquid Chromatography

S T Ingalls, P E Minkler, C L Hoppel, J E Nordlander

J Chromatogr. 1984 Sep 21;299(2):365-76.

PMID: 6548756

Abstract:

The use of 4'-bromo-2-hydroxyacetophenone trifluoromethanesulfonate ester (4'-bromophenacyl triflate) in the preparation of carboxylic acid 4'-bromophenacyl ester derivatives for spectrophotometric detection in high-performance liquid chromatography is described. The reagent is prepared in 66% yield by the reaction of 4'-bromo-2-diazoacetophenone with trifluoromethanesulfonic acid in anhydrous sulfur dioxide and is stable for 3-6 months. Reactions of 10(-6) M carboxylate N,N-diisopropylethylammonium salts with this reagent in acetonitrile at room temperature proceed to completion in 1-5 min. Optimal rates of reaction are obtained with a 10-fold equivalent excess of alkylating agent and 5 equivalents of N,N-diisopropylethylamine present. The process has been applied successfully to mono-, di- and tricarboxylic and sterically hindered carboxylic acids.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP93128042	4-Bromophenacyl trifluoromethanesulfonate		93128-04-2	Price

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