The goal of green chemistry is to eliminate hazardous waste from chemical processes, preventing harm to humans and the environment. We are studying the bromination of indole-3-acetic acid (IAA) to 3-bromooxindole-3-acetic acid (BOAA), a reaction that suffers from poor atom economy and low percent yield. To improve reaction efficiency we broke down the synthetic process and reaction mechanism, and evaluated amides and amidines as Lewis base bromination catalysts. NMR analysis revealed that IAA bromination is a two-step process. Poor regioselectivity in addition of the first equivalent of electrophilic bromine is the critical step, producing a mixture of oxindole products responsible for the poor overall reaction efficiency. We are currently optimizing the synthesis and isolation of oxindole-3-acetic acid, the initial intermediate in BOAA production.

Green chemistry principles in electrophilic bromination: Evaluating amides and amidines as Lewis base catalysts for the regioselective bromination of indole-3-acetic acid

247th National Meeting (2014)

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