Fluorination of α-bromomethyl aryl ketones with fluorohydrogenate-based ionic liquids

• Use of fluorohydrogenate ionic liquids as fluorinating agents is described.
• EMIMF·(HF)2.3 and PYR13F·(HF)2.3 used to fluorinate α-bromomethyl aryl ketones.
• Yields above 80% were obtained under mild conditions.
• Fluorohydrogenate ionic liquids are safer than alternatives fluorinating agents.

Fluorination of α-bromomethyl aryl ketones using fluorohydrogenate-based ionic liquids as fluorinating reagent is described. Reaction of various α-bromomethyl aryl ketones (1a-g) with fluorohydrogenate-based ionic liquids such as EMIMF·(HF)2.3, PYR13F·(HF)2.3 or PYR14F·(HF)2.3 as a fluoride ion source in anhydrous THF led to the formation of the corresponding α-fluoromethyl aryl ketones (2a–g) in very good yield. Compared to alternative fluorinating agents for this reaction, fluorohydrogenate-based ionic liquids are safer to handle and have the potential to be less expensive and more selective.

Reaction of various α-bromomethyl aryl ketones with fluorohydrogenate-based ionic liquids such as PYR13F·(HF)2.3 as in anhydrous THF led to the formation of the corresponding α-fluoromethyl aryl ketones in very good yield.Figure optionsDownload as PowerPoint slide