The goal of green chemistry is to eliminate the use and generation of hazardous chemicals to prevent harm to people and the environment. We have been studying the synthesis of 3-bromooxindole-3-acetic acid (BOAA). BOAA is converted into 3-methyleneoxindole (MOI) which is an inhibitor of cysteine proteases, enzymes that are suspected contributors in diseases such as cancer. The major issues with the BOAA synthesis are poor atom economy and low percent yield. The standard synthesis requires indole-3-acetic acid (IAA), tert-butanol, and N-bromosuccinimide (NBS). We have identified that the bromination of IAA by NBS is responsible for the poor efficiency of this reaction, and have evaluated bromide salts, hydrogen peroxide, and a layered double hydroxide tungstate catalyst for the greener bromination of IAA. Initial testing of this catalyst has given promising results for a more efficient BOAA synthesis.

Chemical sustainability in the bromination of organic compounds: Evaluating a tungstate catalyst in the synthesis of 3-bromooxindole-3-acetic acid, a potential therapeutic agent

245th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.