Related Experiment Video
Updated: Sep 19, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Triphosgene/KF-mediated acyl fluoride synthesis via in situ fluoro(chloro)phosgene
Elsayed M Mahmoud1,2, Mohammed A Marzouk1, Wesam S Shehab3
1Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig 44519, Egypt. EMsalih@pharmacy.zu.edu.eg.
Abstract:
The transformation of carboxylic acids into acyl fluorides via triphosgene-mediated deoxyfluorination utilizing inexpensive potassium fluoride (KF) has been achieved. This method affords a diverse range of acyl fluorides in high yields and exceptional purity. Analysis using 19F NMR spectroscopy reveals that fluorophosgene and chlorofluorophosgene, generated in situ, serve as the reactive intermediates crucial to the conversion process. The protocol exhibits excellent functional group tolerance, enabling late-stage modification of biologically relevant compounds, and is scalable for both lab and industrial use. Acyl fluorides also proved valuable as precursors for amides, organic intermediates, and fluorine donors.
More Related Videos
09:58Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
Base-Promoted α-Halogenation of Aldehydes and Ketones