Water → HCID 86631570, compound

HRID 1880260Notes

Reaction equation

HRID 1880260 reaction equation
O1CCCC1.[Br-].[F:7][C:8]([F:13])([F:12])[C:9]([Zn+])=[CH2:10].Br[C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([O:22][CH:23]([F:25])[F:24])=[C:17]([Cl:26])[CH:16]=1.O>CN(C)C=O>[Cl:26][C:17]1[CH:16]=[C:15]([C:9]([C:8]([F:13])([F:12])[F:7])=[CH2:10])[CH:20]=[C:19]([Cl:21])[C:18]=1[O:22][CH:23]([F:25])[F:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 668657425-Bromo-1,3-dichloro-2-(difluoromethoxy)benzeneHCID 178477747HCID 178477747, compound

Product 1

HCID 86631570HCID 86631570, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 21 mL of a 1M tetrahydrofuran solution of 1-trifluoromethylethenyl zinc bromide prepared according to a method described in the literatures, a solution of 2.4 g of 4-bromo-2,6-dichloro(difluoromethoxy)benzene in 12 mL of N,N-dimethylformamide was added, and tetrahydrofuran was distilled off under reduced pressure. To the remaining N,N-dimethylformamide solution, 0.23 g of dichlorobis(triphenylphosphine) palladium (II) was added and the resultant mixture was stirred at 100° C. for 3 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 diethyl ether (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 hexane to obtain 1.8 g of the objective substance as a brown oily substance.

Workup

  1. distillationtetrahydrofuran was distilled off under reduced pressure
  2. additionTo the remaining N,N-dimethylformamide solution, 0.23 g of dichlorobis(triphenylphosphine) palladium (II) was added
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. temperatureto be cooled down to room temperature
  6. extractionthe resultant mixture was extracted with diethyl ether (100 mL×1)
  7. washThe organic phase was washed with water
  8. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resultant residue was purified by silica gel column chromatography
  11. washeluting with hexane
  12. customto obtain 1.8 g of the objective substance as a brown oily substance

Sources & evidence

ORD record
ord-2aa98a461fd64f7a8dbbb2af06e61cd7
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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