Water → HCID 69800188, compound

HRID 1268291Notes

Reaction equation

HRID 1268291 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:21])[CH:11]=[CH:12][C:13]1[CH:18]=[C:17](Br)[CH:16]=[C:15](Br)[CH:14]=1)[CH3:8].[C:22]1([C:28]#[CH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:7]([O:9][C:10](=[O:21])[CH:11]=[CH:12][C:13]1[CH:18]=[C:17]([C:29]#[C:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=[C:15]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:14]=1)[CH3:8]

Participants

8

Reactant 4

HCID 962WaterHCID 10821PhenylacetyleneHCID 11430Potassium CarbonateHCID 69800801HCID 69800801, compound

Product 1

HCID 69800188HCID 69800188, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of potassium carbonate (2.1 g, 15.2 mmol), tetra-N-butylammonium bromide.(0.75 g, 2.4 mmol) and palladium(II) acetate (75 mg, 0.33 mmol) in dry DMF (8 ML), under nitrogen, was stirred for 10 min. 3-(3,5-Dibromophenyl)-acrylic acid ethyl ester (1.2 g, 3.6 mmol) was added and the mixture cooled on ice. Phenylacetylene (4.0 mL, 36.0 mmol) was added and the mixture stirred at room temperature for 7 days. The reaction mixture was added water and the product extracted with ethyl acetate (×3). The combined organic phases were dried and concentrated in vacuo to give crude 3-(3,5-bis-phenylethynyl-phenyl)-acrylic acid ethyl ester.

Workup

  1. temperaturethe mixture cooled on ice
  2. extractionthe product extracted with ethyl acetate (×3)
  3. customThe combined organic phases were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d30dcd07ebd42ee9ea5d7254963dccc
Source dataset
uspto-grants-2003_04
Patent number
US06555577B1

Reaction notes

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