Diethyl Ether → 2-[2-Fluoro-4-(furan-2-ylmethyl)-phenyl]propionic acid

Participants

Reaction Steps

Compound 20 (0.88 g, 3.2 mmol) and 2-furan boronic 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 heated to reflux for 3 hours. After cooling to room temperature and adding ether (50 mL) to the solution, the organic layer was washed with water (30 mL) and dried (over magnesium sulfate), and the solvent was distilled off. 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 0.36 g (43%) of compound (21a) of interest as white solid.

Provenance & Evidence