Mechanochemical fluorination of naproxen and its salts with F-TEDA-BF4

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Resumo

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.

Sobre autores

G. Borodkin

Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences

Email: gibor@nioch.nsc.ru

I. Elanov

Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences

V. Shubin

Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences

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