Fluoroformates from carbonyl chloride fluoride

Tri-n-hutylamine Reactions of carbonyl halides with cyclic ethers o>-Chloralkyl fluoroformates from carbonyl chloride fluoride... 

An alternative means of technical-scale access to fluoroarenes is the fluoroformate method. Starting from the corresponding phenol a fluoroformate is generated by reaction with carbonyl chloride fluoride and subsequently catalytically decarboxy-lated to the aryl fluoride, in the gas phase, by contact with hot platinum [80] (Scheme 2.30). A newer, greener variant of the fluoroformate process has recently been introduced by Rhodia. In this the fluoroformate is formed by the (catalyzed) reaction of the phenol with COj in HF, and the expensive platinum catalyst is replaced by an aluminum-based material. 

Chloroformates, carbonyl chlorides and acid chlorides are converted into the corresponding fluorides 1 in excellent yield upon treatment with potassium fluoride in the presence of 18-crown-6 at room temperature. Fluoroformates are also synthesized from chloroformates by fluorination with potassium fluoride in acetylacetone at 60"C under UV irradiation, with potassium fluoride in nitrobenzene,- with potassium fluoride in the absence of a solvent at temperatures in the range 100-250 and with thallium(I) fluoride. 

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