Sodium Carbonate → 2-[2-Fluoro-4-(furan-3-ylmethyl)-phenyl]propionic acid

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Reaction Steps

Compound 20 (0.88 g, 3.2 mmol) and 3-furanboronic acid (0.54 g, 4.8 mmol) were dissolved in tetrahydrofuran (12 mL) and a 2 M-aqueous solution (4.0 mL) of sodium carbonate. To this solution, trans-bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) [trans-PdBr(N-Succ)(PPh3)2] (25.9 mg, 1.0 mol %) was added and treated in the same manner as in Example 11. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (20:1) solution followed by conventional hydrolysis with potassium hydroxide to give 0.46 g (55%) of compound (22a) of interest as white solid.

Provenance & Evidence