Trifluoroperacetic Acid

Process Safety Considerations for the Supply of a High-Energy Oxadiazole IDO1-Selective Inhibitor

“…After some additional evaluation, it was determined that either TFA/urea hydrogen peroxide (UHP) or TFA/hydrogen peroxide afforded the cleanest reaction profile. Both sets of conditions are believed to proceed through the same reactive species (pertrifluoroacetic acid (PTFA) − ), and therefore, the selection of conditions was based on more practical considerations. Further development led to the conclusion that the latter set of conditions using hydrogen peroxide was likely easier to operate because hydrogen peroxide can be dosed continuously more easily than UHP (a solid), which in turn means that the individual reaction steps could be better controlled, thus avoiding potential runaway exotherms.…”

Direct Acetoxylation of Arenes

“…In an attempt to introduce an acetoxyl group to arenes, we searched the related methods in the literature and noticed that the results derived from applying trifluoroacetic acid (TFA), trifluoroacetic anhydride (TFAA), or peroxytrifluoroacetic acid to arenes are varied and interesting. For example, the reaction of anisole and peroxytrifluoroacetic acid, prepared in situ from TFA or TFAA with hydrogen peroxide, gave the hydroxylation products (eq ). With excess peroxytrifluoroacetic acid in TFA, alkylbenzenes were oxidized to form aliphatic carboxylic acids (eq ).…”