Cesium fluoride → 4-(3-Ethyl-4'-fluorobiphenyl-4-yl)-2,2,6-trimethylpyran-3,5-dione

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Reaction Conditions

Reaction Steps

To a mixture of 4-(4-bromo-2-ethylphenyl)-2,2,6-trimethylpyran-3,5-dione (0.5 g, 1.48 mmol), cesium fluoride (0.70 g, 4.4 mmol), 4-fluorophenylboronic acid (0.31 g, 2.23 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (0.19 g, 0.23 mmol) is added degassed dimethoxyethane (15 ml) and the resulting suspension is stirred under nitrogen for 45 minutes then heated at 80° C. for 24 hours. After cooling to room temperature the reaction mixture is acidified with 1N aqueous hydrochloric acid. The mixture is extracted with ethyl acetate (3×25 ml) and then all organic fractions are combined, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to afford 4-(3-ethyl-4′-fluorobiphenyl-4-yl)-2,2,6-trimethylpyran-3,5-dione (0.27 g) as a white solid.

Provenance & Evidence