Water → HCID 69800188, compound

HRID 984349Notes

Reaction equation

HRID 984349 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. stirringthe mixture stirred at room temperature for 7 days
  3. extractionthe product extracted with ethyl acetate (×3)
  4. customThe combined organic phases were dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b103f91449f24171ae041186cdad8518
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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