Darryl D. DesMarteau, Lawrence A. Ford, and Monika Mujkic. Advanced Material Research Laboratory, Anderson, SC
One area of current interest is the use of the sulfonimide function to prepare fluorinated ionic liquids for the application as electrolytes in secondary lithium batteries [1]. 1,3,5-Tris(α,β,β-trifluorovinyl)benzene is a versatile starting material for trifunctional ionic liquids and can be obtained by the reaction of trifluorovinylzincbromide with 1,3,5-tribromobenzene in the presence of catalytic amounts of tetrakis(triphenylphosphine)palladium [2]. Subsequent bromination and halogen-halogen-exchange of the secondary bromine atom leads to tris(2-bromo-1,1,2,2-tetrafluoroethyl)benzene. A common method for bromine-fluorine-exchange is the Swarts reaction. Antimony trifluoride and a catalytic amount of chlorine gas or antimony pentachloride were used. Compared to the monofunctional 2-bromo-1,1,2,2-tetrafluoroethylbenzene, which was used as a model compound, the fluorination of the trifunctional compound requires more harsh conditions. [1] P. Hallac, O. Geiculescu, R. Rajagopal, C. Topping, S. Craeger, D. DesMarteau, Chimica Oggi (Chemistry Today) 2007, submitted. [2] L. A. Ford, D. D. DesMarteau, Chem. Commun. 2003, 2596-2597.
