Water → 1-Bromo-4-chloro-2-(difluoromethoxy)benzene

Temperature

100 °C

The title compound was prepared according to the procedure disclosed in Published PCT Patent Application No. WO2011/003065 A2. To a solution of 2-bromo-5-chlorophenol (4.34 g, 20.92 mmol) (the oil from above) in N,N-dimethylformamide (21.8 mL, 20.9 mmol) was added sodium chlorodifluoroacetate (7.34 g, 48.1 mmol), cesium carbonate (9.54 g, 29.3 mmol), and water (2.18 mL, 20.9 mmol). The reaction was stirred at 100° C. for 16 h. The reaction was cooled to room temperature and partitioned between EtOAc (100 mL) and water (50 mL). The aqueous layer was extracted with EtOAc (2×70 mL). The organic layers were combined and washed with water (2×50 mL), 10% aq. citric acid (1×30 mL), brine, dried over MgSO4, filtered, and concentrated to afford 1-bromo-4-chloro-2-(difluoromethoxy)benzene (4.35 g, 16.9 mmol). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.30 (dd, J=2.3, 8.6 Hz, 1H), 7.37 (t, J=73 Hz, 1H), 7.49 (dt, J=2.40, 0.81 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H).

1. customThe title compound was prepared
2. temperatureThe reaction was cooled to room temperature
3. custompartitioned between EtOAc (100 mL) and water (50 mL)
4. extractionThe aqueous layer was extracted with EtOAc (2×70 mL)
5. washwashed with water (2×50 mL), 10% aq. citric acid (1×30 mL), brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-d7c356dc8171456fb7b999f666237038

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012443B2