3,4-Dichlorophenol → 2-[5-(3,4-Dichlorophenoxy)-2-ethylphenyl]cyclopentane-1,3-dione

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(5-bromo-2-ethylphenyl)cyclopentane-1,3-dione (0.200 g, 0.71 mmol), 3,4-dichlorophenol (0.577 g, 3.56 mmol), cesium carbonate (0.502 g, 1.42 mmol), copper triflate (13 mg, 0.04 mmol) and activated (powdered) 5 Å molecular sieves (0.400 g) is added anhydrous toluene (2.5 ml). The reaction mixture is purged with nitrogen then heated at 160° C. for 1 hour under microwave irradiation. After cooling to room temperature dichloromethane is added and mixture is quenched with 2M aqueous hydrochloric acid then filtered. The organic phase is concentrated under reduced pressure to give a crude oil which is purified by preparative reverse-phase HPLC to afford 2-[5-(3,4-dichlorophenoxy)-2-ethylphenyl]cyclopentane-1,3-dione.

Provenance & Evidence