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

HRID 1187947Notes

Reaction equation

HRID 1187947 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)benzeneYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 25.0 g of 3,5-dichlorophenyl boric 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 stirred under reflux with heat for 3 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, 500 mL of ice water was added, and extracted with ethyl acetate (500 mL×1). The organic phase was washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with hexane to obtain 25.7 g of the aimed product as colorless oily substance.

Workup

  1. temperatureunder reflux
  2. temperaturewith heat for 3 hours
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. extractionextracted with ethyl acetate (500 mL×1)
  6. washThe organic phase was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-49c28d33ff0a49c3aad52d6c89fd3ce6
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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