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

Temperature

160 °C

To a mixture of 4-chlorophenol (0.473 g, 3.69 mmol), cesium carbonate (0.521 g, 1.48 mmol), copper triflate (0.013 g, 0.04 mmol) and powdered 5 Å molecular sieves (0.400 g) is added a solution of 2-(5-bromo-2-trifluoromethoxyphenyl)cyclopentane-1,3-dione (0.249 g, 0.74 mmol) in anhydrous toluene (3.5 ml). The mixture is flushed with nitrogen and heated at 160° C. for 1 hour under microwave radiation, then for a further 1 h at 170° C. After cooling to room temperature the crude product is partitioned between dichloromethane (5 ml) and 2M hydrochloric acid (5 ml), and the organic phase is separated then concentrated in vacuo. The residue is then purified by flash column chromatography on silica gel (ethyl acetate/iso-hexane eluant) to afford 2-[5-(4-chlorophenoxy)-2-trifluoromethoxyphenyl]cyclopentane-1,3-dione as a white solid.

1. customThe mixture is flushed with nitrogen
2. temperatureAfter cooling to room temperature the crude product
3. customis partitioned between dichloromethane (5 ml) and 2M hydrochloric acid (5 ml)
4. customthe organic phase is separated
5. concentrationthen concentrated in vacuo
6. customThe residue is then purified by flash column chromatography on silica gel (ethyl acetate/iso-hexane eluant)

ORD record

ord-af09a8cffd5a4e75982d29490f4cbe5b

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895474B2