4-Fluorophenol → 2-(4-Fluorophenoxy)-terephthalic acid dimethyl ester

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Reaction Steps

To a solution of 4-fluorophenol (1.25 g, 11.15 mmol) in toluene (50 mL) was added cesium carbonate (6.10 g, 18.7 mmol) and the mixture was stirred for 15 min at rt. 2-Iodoterephthalic acid dimethyl ester (3.0 g, 9.37 mmol) and tetrakisacetonitrilecopper hexafluorophosphate (435 mg) were added, and the mixture was heated to reflux for 18 h. The mixture was allowed to cool to rt and poured into an ice-cold saturated ammonium chloride solution. The organic layer was separated, washed with a saturated potassium carbonate solution and brine, dried over magnesium sulfate, filtered, and evaporated. The residue was purified via flash column chromatography (elent gradient 1% to 20% EtOAc in heptane) to yield 1.25 g (43.8%) of title compound 2-(4-fluorophenoxy)-terephthalic acid dimethyl ester, 1e. MS m/z (MH+) 305.0.

Provenance & Evidence