Celebration of Scholars
#36: Radical Fluorination of an Ibuprofen Derivative
Name:
Angelina Coolidge
Major: Chemistry
Hometown: Sturtevant, WI
Faculty Sponsor:
Other Sponsors:
Type of research: Independent research
Abstract
Radical halogenation is a reaction valuable in various organic syntheses that substitutes a hydrogen for a halogen. Radical halogenation is often carried out using bromine due to its high selectivity and stability. However, radical fluorination is more attractive in pharmaceutical research due to fluorine’s ability to enhance the bioavailability and stability of drugs. Here we show the selective radical fluorination of the secondary benzylic position of ibuprofen methyl ester via the use of an electrophilic fluorine source, with and without a catalyst, and under 365 nm UV light. A variety of reaction variables were explored to find the optimal conditions for conducting this reaction. Ultimately, we determined that 1.5 equivalents of N-fluorobenzenesulfonimide, 0.5 mL of acetonitrile as the solvent, a blacklight centered at 365 nm, and letting the reaction run for 24 hours on a 0.1 mmol scale provided the fluorinated product with the highest yield. Current efforts are focused on developing a method to purify the product and mechanistic experiments to confirm the mechanism of the reaction.Submit date: March 28, 2023, 11:16 a.m.