Affiliation:
1. Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences
Abstract
The mechanochemical fluorination of naproxen and its salts (Li, Na and K) using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™, F-TEDA-BF4) has been studied. The reaction of naproxen with an excess of Selectfluor gives 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalene-2-yl)propionic acid in high yield. The use of a small amount of Al2O3, SiO2, M2CO3 (M = Na, K, Rb, Cs), ionic liquids (ILs), crown ethers, and N-bases enhances the rate of reaction of naproxen with Selectfluor and increases the proportion of the monofluorination product compared to the difluorination product.
Publisher
The Russian Academy of Sciences