Water → 5-Bromo-1,3-dichloro-2-(difluoromethoxy)benzene

To a solution of 2.3 g of 4-bromo-2,6-dichlorophenol in 25 mL of acetonitrile, 1.3 g of potassium carbonate and 3.8 g of ethyl bromodifluoroacetate were added and the resultant mixture was stirred while heating the mixture to reflux for 4 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and charged into 100 mL of water and the resultant mixture was extracted with ethyl acetate (100 mL×1). The organic phase was washed with water and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:4) to obtain 2.4 g of the objective substance as a yellow oily substance.

1. temperaturewhile heating the mixture
2. temperatureto reflux for 4 hours
3. customAfter the completion of the reaction
4. waitthe reaction mixture was left
5. extractionthe resultant mixture was extracted with ethyl acetate (100 mL×1)
6. washThe organic phase was washed with water
7. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
8. distillationthe solvent was distilled off under reduced pressure
9. customThe resultant residue was purified by silica gel column chromatography
10. washeluting with ethyl acetate-hexane (1:4)
11. customto obtain 2.4 g of the objective substance as a yellow oily substance

ORD record

ord-5d402632bb754b91a7fd1c6bc7b238ba

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318757B2