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31.1.1.1.5 Method 5: Reaction with Cesium Fluoroxysulfate

DOI: 10.1055/sos-SD-031-00002

Sandford, G.Science of Synthesis, (20073141.

Cesium fluoroxysulfate (CsSO4F, 21) is a white, crystalline solid that can be prepared by fluorination of cesium sulfate with elemental fluorine and stored at 0°C for about 2 weeks in polyethylene vessels.[‌81‌] Acetonitrile is generally used as the solvent for reactions involving cesium fluoroxysulfate (Scheme 16), and a Lewis acid catalyst, usually boron trifluoridediethyl ether complex, is sometimes added to enhance selectivity in the formation of the fluoroarene product 23. Reactions with phenol derivatives, e.g. 4-tert-butylphenol (22, Ar1=5-t-Bu-2-HOC6H3), show a high ortho selectivity, whereas fluorination of toluene leads to a mixture of fluorotoluene isomers. Highly methylated benzene derivatives, such as 1,2,4,5-tetramethylbenzene (durene), are fluorinated on their methyl side chains.[‌82‌]

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