Regiospecific synthesis of 1-methyl-4-vinylimidazole

CHED 319

Brett Granger, bag6786@rit.edu, Christina G. Collison, cgcsch@rit.edu, and Thomas W. Smith, twssch@rit.edu. Department of Chemistry, Rochester Institute of Technology, 85 Lomb Memorial Dr, Rochester, NY 14623
1-methyl-4-vinylimidazole is a 5-membered aromatic compound which is being synthesized as a precursor to 1,3-dialkyl-4- and -5-vinylimidazolium salts. These salts are room temperature ionic liquids (RTILs), which can be polymerized. Polymerizable RTILs are of interest because of their possible use as transducers, and in membranes in electrochemical devices and fuel cells. An efficient synthesis of the known 1-methyl-4-vinylimidazole monomer is described as well as the optimization of the final Pd-catalyzed coupling step.