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

4-bromo-2-chlorophenol (1.0 g, 4.8 mmol) was dissolved in DMF (35 ml) and water (5 ml) was added followed by sodium chloro(difluoro)acetate (2.0 g, 12 mmol) and cesium carbonate (3.1 g, 9.6 mmol). The mixture was stirred for 15 minutes at room temperature and then heated to 100° C. for 2 hours under nitrogen. The mixture was partitioned between water (50 ml) and tBuOMe (50 ml). The organic phase was separated, washed brine, dried over sodium sulphate, filtered, and concentrated in vacuo to give a crude product. The crude product was purified by silica gel chromatography eluting with 0-30% EtOAc in heptanes to give a title compound (0.83 g, 67% yield) as colourless oil.

1. temperatureheated to 100° C. for 2 hours under nitrogen
2. customThe mixture was partitioned between water (50 ml) and tBuOMe (50 ml)
3. customThe organic phase was separated
4. washwashed brine
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give a crude product
9. customThe crude product was purified by silica gel chromatography
10. washeluting with 0-30% EtOAc in heptanes

ORD record

ord-01fedac981e3476fb5b29d048fe4228b

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685977B2