4-Chlorophenol → 2-[5-(4-Chlorophenoxy)-2-cyclopropylphenyl]cyclopentane-1,3-dione

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(5-bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione (0.254 g, 0.062 mmol), 4-chlorophenol (0.400 g, 3.11 mmol), cesium fluoride (0.440 g, 1.25 mmol) and copper (II) triflate (11 mg, 0.03 mmol) is added 4 Å powdered molecular sieves (0.40 g) and anhydrous toluene (3.5 ml). This mixture is then heated at 160° C. for 1 hour under microwave irradiation, allowed to cool to room temperature then quenched with 2M hydrochloric acid. The reaction mixture is extracted with dichloromethane (×3), then the combined organics are washed with brine, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by preparative reverse phase HPLC to afford 2-[5-(4-chlorophenoxy)-2-cyclopropylphenyl]cyclopentane-1,3-dione as a white solid.

Provenance & Evidence