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

HRID 2386160Notes

Reaction equation

HRID 2386160 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Br[C:13]([C:15]([F:18])([F:17])[F:16])=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([C:15]([F:18])([F:17])[F:16])=[CH2:14])[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 27343313,5-Dichlorophenylboronic 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-dichlorophenyl boronic 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 dichlorobis(triphenylphosphine) palladium (II) were added, and the resultant reaction 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 down to room temperature and 500 mL of ice water was added to the reaction mixture, followed by extracting the reaction mixture with ethyl acetate (500 mL×1). Subsequently, the organic phase was washed with water and was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with hexane to obtain 25.7 g of the objective substance as a colorless oily substance.

Workup

  1. customthe resultant reaction mixture
  2. temperaturewhile heating the mixture
  3. temperatureto reflux for 3 hours
  4. customAfter the completion of the reaction
  5. waitthe reaction mixture was left
  6. extractionby extracting the reaction mixture with ethyl acetate (500 mL×1)
  7. washSubsequently, the organic phase was washed with water
  8. dry with materialwas dried over anhydrous sodium sulfate
  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 25.7 g of the objective substance as a colorless oily substance

Sources & evidence

ORD record
ord-e97aff0157184380bd8266cd4c098a01
Source dataset
uspto-grants-2012_09
Patent number
US08268754B2

Reaction notes

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