Lithium Chloride → 4-Chloro-2-(trifluoromethoxy)phenol

Temperature

100 °C

A solution of copper(II)chloride dihydrate (37.2 mmol, 6.34 g) and lithium chloride (18.6 mmol, 788 mg) in DMF (60 mL) was heated to 80° C. before the addition of 2-(trifluoromethoxy)phenol (18.6 mmol, 4 g) dropwise. The reaction was stirred at 100° C. for 72 hours. After cooling, the reaction mixture was partitioned between EtOAc (60 mL) and water (120 mL), extracted with EtOAc (60 mL). The organic layer was washed with water (60 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting product with a gradient of 0-100% DCM in heptane to yield the title compound as a waxy solid (637 mg, 10%). This was used in the next step with no further purification.

1. temperatureAfter cooling
2. customthe reaction mixture was partitioned between EtOAc (60 mL) and water (120 mL)
3. extractionextracted with EtOAc (60 mL)
4. washThe organic layer was washed with water (60 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude material was purified by silica gel column chromatography
9. washeluting product with a gradient of 0-100% DCM in heptane

ORD record

ord-efd2bdc916584161a4de1fc4cfe86b96

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685977B2