3,5-Dimethoxyphenol → 2-(3,5-Dimethoxyphenoxy)-6-fluorophenyl acetic acid

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Reaction Conditions

Reaction Steps

N,N-Dimethylformamide (20 ml) was added to 2-chloro-6-fluorophenyl acetic acid (3.77 g), 3,5-dimethoxyphenol (3.08 g), potassium carbonate (5.52 g), copper iodide (950 mg) and copper (250 mg), for stirring at 120° C. for 20 hours. The resulting reaction solution was partitioned with ethyl acetate and dilute hydrochloric acid, and the organic phase was washed in water and in a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, to distill off the solvents under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=7:3), to recover 2-(3,5-dimethoxyphenoxy)-6-fluorophenyl acetic acid (5.27 g; yield of 86%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

Provenance & Evidence