O-fluorobenzoic acid

A new study has been reported of the hydrolysis of the p-tolyldiazonium cation using a combination of carbon kinetic isotope effects, theoretical calculations, and dynamics trajectories. Overall, the results are in best accord with a process at the boundary between. S N 1 and. S N2Ar mechanisms.1 There has been a kinetic study of the thermolysis of o-carboxybenzenediazonium fluoride to give o-fluorobenzoic acid in liquid hydrogen fluoride under pressure.2... 

AROMATIC SUBSTITUTION - Reaction of oxazolines from o-fluorobenzoic acids with organometalllc reagents results in net displacement of halogen. Hydrolysis of the heterocycle affords the substituted benzoic acld. ... 

In 2010, Chen and co-workers [134] developed the first organocatalytic asymmetric conjugate addition of a, 3-unsaturated aldehydes via iminium catalysis. In the presence of diarylprolinol silylether 7 and o-fluorobenzoic acid (OFBA), the reaction proceeded well to afford the highly valued adducts with excellent enantioselectivities and with up to outstanding diastereoselectivities (Scheme 5.67). To emphasize the synthetic utility of the reaction, a number of natural-product-like or drug-like molecules with versatile skeletons have been efficiently constructed from the corresponding Michael adducts. 

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