Organic Fluorine Compounds. Part XLII. The Reaction of Amides of α‐Bromoacids with Potassium Fluoride

Abstract

The reaction of potassium fluoride with α‐bromocarboxylic acid anilides, substituted in the α‐ or β‐position, causes dehydrohalogenation and gives α, β‐unsaturated anilides. Long‐chain α,α′‐dibromodicarboxylic acid (>C8) anilides give in the same reaction essentially α,αprime;‐di‐fluorocarboxylic acid anilides.

Attaching the Fluorine Atom to Organic Molecules Using BrF3 and Other Reagents Directly Derived from F2

“…These two types of side reactions become dominant whenever Ror β-branched carboxylic acids were the target molecules. 56 These limitations encouraged development of alternative, specific multistep routes, which usually resulted in low overall yields.…”

“…Because of the basicity of the fluoride ion, however, such an approach resulted in elimination reactions or various rearrangements along with the desired α-fluoroacids. These two types of side reactions become dominant whenever α- or β-branched carboxylic acids were the target molecules . These limitations encouraged development of alternative, specific multistep routes, which usually resulted in low overall yields.…”