Synthesis of nucleophilic fluoride reagent based on imidazolium polyfluoride was accomplished in aqueous solution by ion exchange with hydrofluoric acid as cheap source of fluoride ions. With our goal of bonding the imidazolium based fluoride reagents on the polymeric solid support a substituted 2-benzylimidazolium polyfluoride was synthesised to check for reactivity of bulky imidazolium cation. By chlorination in aqueous solution of sodium hypochlorite an easily approachable synthesis of 2-chloro substituted imidazolium polyfluoride, derivative of PhenoFluor reagent, was also accomplished. It is air-stable and showes remarkable stabillity towards hydrolysis even at elevated temperatures and alkaline solution. Deoxyfluorination of heteroaromatic phenol and carboxylic acid under non-inert conditions was achieved without use of external fluoride ions.
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