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Mechanochemical Fluorination of Naproxen and Its Salts with F–TEDA–BF4

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Abstract

The mechanochemical fluorination of naproxen and its salts (Li, Na, and K) with 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor, F–TEDA–BF4) was studied. The reaction of naproxen with an excess of Selectfluor gives 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalen-2-yl)propionic acid in high yield. Small additives of Al2O3, SiO2, M2CO3 (M = Na, K, Rb, Cs), ionic liquids (ILs), crown ethers, and N-bases accelerate the reaction of naproxen with Selectfluor and increases the monofluorination/difluorination product ratio.

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ACKNOWLEDGMENTS

The authors express their gratitude to the Chemical Service Center for Collective Use, Siberian Branch, Russian Academy of Sciences (SB RAS), for measuring the NMR spectra (Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Novosibirsk).

Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 20-03-00700A).

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Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    G. I. Borodkin, I. R. Elanov & V. G. Shubin

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  1. G. I. Borodkin
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  2. I. R. Elanov
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  3. V. G. Shubin
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Corresponding author

Correspondence to G. I. Borodkin.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 11, pp. 1418–1426 https://doi.org/10.31857/S0514749223110034.

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Borodkin, G.I., Elanov, I.R. & Shubin, V.G. Mechanochemical Fluorination of Naproxen and Its Salts with F–TEDA–BF4. Russ J Org Chem 59, 1858–1866 (2023). https://doi.org/10.1134/S1070428023110039

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