HCID 66783884, compound → HCID 86611476, compound

HRID 1096133Notes

Reaction equation

HRID 1096133 reaction equation
[Br-].[F:2][C:3]([F:8])([F:7])[C:4]([Zn+])=[CH2:5].[Br:9][C:10]1[C:11]([O:17][CH:18]([F:20])[F:19])=[C:12](I)[CH:13]=[CH:14][CH:15]=1>O1CCCC1.Cl>[Br:9][C:10]1[C:11]([O:17][CH:18]([F:20])[F:19])=[C:12]([C:4]([C:3]([F:8])([F:7])[F:2])=[CH2:5])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 66783884HCID 66783884, compoundHCID 178477747HCID 178477747, compound

Product 1

HCID 86611476HCID 86611476, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of a solution of 1-trifluoromethylethenyl zinc bromide prepared according to the method described in documents in 1M tetrahydrofuran, 1.0 g of 3-bromodifluoromethoxy-1-iodobenzene and 0.05 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under reflux with heat for 2 hours. After the completion of the reaction, the reaction mixture was poured in 20 ml of diluted hydrochloric acid, extracted with ethyl acetate (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was dissolved in hexane, and high polar impurities were excluded by treating with silica gel to obtain 0.77 g of crude aimed product as colorless oily substance. The resulting product was used as such without purification for the next step.

Workup

  1. temperatureunder reflux
  2. temperaturewith heat for 2 hours
  3. customAfter the completion of the reaction
  4. extractionextracted with ethyl acetate (50 ml×1)
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. dissolutionThe residue was dissolved in hexane
  8. additionby treating with silica gel

Sources & evidence

ORD record
ord-09f504ce9aaa43a38d765095949019d5
Source dataset
uspto-grants-2012_03
Patent number
US08138213B2

Reaction notes

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