Potassium Carbonate → 1,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

HRID 1642749Notes

Reaction equation

HRID 1642749 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OB(O)O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Br[C:14]([C:16]([F:19])([F:18])[F:17])=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([C:16]([F:19])([F:18])[F:17])=[CH2:15])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 222835213,5-Dichlorophenylboric acid

Product 1

HCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 25.0 g of 3,5-dichlorophenylboric acid in 200 mL of tetrahydrofuran and 100 mL of water, 27.5 g of 2-bromo-3,3,3-trifluoropropene, 38.0 g of potassium carbonate and 1.84 g of dichloro-bis(triphenylphosphine) palladium (II) were added and the resultant mixture was stirred while heating the mixture to reflux for 3 hours. After the completion of the reaction, the reaction mixture was left to be cooled to room temperature and 500 mL of ice water was added to the mixture, followed by extracting the mixture with ethyl acetate (500 mL×1). The organic phase was cleaned with water and then dried over anhydrous sodium sulfate, and the solvent was distilled off from the organic phase under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography eluting with hexane to obtain 25.7 g of the objective substance as a colorless oily substance.

Workup

  1. temperaturewhile heating the mixture
  2. temperatureto reflux for 3 hours
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. extractionby extracting the mixture with ethyl acetate (500 mL×1)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off from the organic phase under reduced pressure
  8. customby purifying the resultant residue by silica gel column chromatography
  9. washeluting with hexane
  10. customto obtain 25.7 g of the objective substance as a colorless oily substance

Sources & evidence

ORD record
ord-30846cbd29dc43ab89937ff01c03c7bf
Source dataset
uspto-grants-2012_02
Patent number
US08119671B2

Reaction notes

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