Convenient routes to 2-aryl-2-fluoropropionic acids: Synthesis of monofluorinated analogues of (±)-ibuprofen, (±)-naproxen and related compounds

Article abstract of DOI:10.1016/0040-4020(96)00758-2

The synthesis of α-fluorinated arylpropionic acids 5 as analogues of the nonsteroidal anti-inflammatory agents (NSAIDs) flurbiprofen 1, ibuprofen 3 and naproxen 4 is accomplished by the oxidation of the corresponding primary alcohols 9. The latter are accessible on two different pathways showing their general applicability by variation of the aromatic moiety. Furthermore the influence of the fluorine substituent towards the conformation of the acid moiety in the crystal lattice is shown by comparative X-ray studies of compound 5c.