Potassium Acetate → 4-Chloro-2-(difluoromethoxy)phenol

To a solution of 4-chloro-2-(difluoromethoxy)bromobenzene (Preparation 27, 200 mg, 0.63 mmol) in THF (6 mL) was added bis-neopentylglycolatodiboron (149 mg, 0.660 mmol), potassium acetate (191 mg, 1.88 mmol) and Pd(dppf)Cl2 (23 mg, 0.031 mmol). The reaction mixture was heated to reflux for 4 hours before cooling and diluting with EtOAc and water. The organic layer was collected, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in acetone (6 mL) and treated with a solution of oxone (1.64 g, 2.54 mmol) in water (6 mL). The reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with diethyl ether (10 mL) and water (5 mL). The organic layer was collected, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-15% diethyl ether in DCM to afford the title compound.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 4 hours
3. temperaturebefore cooling
4. customThe organic layer was collected
5. washwashed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. dissolutionThe residue was dissolved in acetone (6 mL)
9. customThe organic layer was collected
10. washwashed with brine
11. dry with materialdried over Na2SO4
12. concentrationconcentrated in vacuo
13. customThe residue was purified
14. washeluting with 0-15% diethyl ether in DCM

ORD-Eintrag

ord-3e0d3f3b75c640f580e90c4fb4df631f

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09067922B2