Synthesis of ethyl-4-phenylbenzoate via aqueous Suzuki coupling: Development and implementation of a novel green chemistry experiment for the undergraduate organic chemistry laboratory

CHED 486

Nancy E. Costa, ncosta@mail.une.edu, Joseph M. Simard, Christopher A. Syvinski, and Amy M. Deveau, adeveau@une.edu. Chemistry & Physics Department, University of New England, College of Arts and Sciences, 11 Hills Beach Road, Biddeford, ME 04005
Suzuki couplings are powerful chemical reactions commonly employed in academic and industrial research settings to generate functionalized biaryls. We have developed a discovery-based lab for the organic chemistry undergraduate laboratory that explores green Suzuki coupling using water as a solvent, and exposes students to the professional responsibilities of a pharmaceutical researcher. Specifically, students take on the role of a medicinal chemist striving to identify the greenest and most cost-effective method out of three proposed synthetic approaches to make ethyl-4-phenylbenzoate, 1. Biaryl 1 demonstrates promise as a lead compound in the discovery of new non-steroidal anti-inflammatory drugs, and scale-up of this compound is necessary for future studies. In our work, the development and implementation of green aqueous Suzuki coupling experiments in a traditional introductory organic chemistry course is described.