While electrophilic aromatic substitutions are common undergraduate experiments, the use of fluorine as the electrophile has not typically been studied because of safety issues involving typical fluorine sources. To incorporate this interesting and somewhat unexpected reaction (electrophilic aromatic fluorination) into the undergraduate curriculum, we have developed an experiment using a safe and readily available fluorine source (F-TEDA; SelectfluorTM). We have explored the reaction using anisole and a series of acetanilides. A mixture of 2-, 4-, and 2,4-difluoro substitution products are obtained. We have used 19F NMR to readily analyze the product distribution. The experiment has been done in several lab cycles with the undergraduate students learning about fluorine NMR and its utility in analyzing product mixtures.

Electrophilic fluorination of aromatics: The use of 19F-NMR spectra for the analysis of mixtures

2019 Spring National Meeting

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