Potassium Fluoride → 4'',4'''-Bis(dibutoxyphosphoryl)-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']-sexithiophene

HRID 1662894Notes

Reaction equation

HRID 1662894 reaction equation
I[C:2]1([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]=[CH:4][S:3]1.C([Sn](CCCC)(CCCC)[C:17]1[S:21][C:20]([C:22]2[S:23][C:24]([Sn](CCCC)(CCCC)CCCC)=[CH:25][C:26]=2[P:27]([O:34][CH2:35][CH2:36][CH2:37][CH3:38])([O:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:28])=[CH:19][C:18]=1P(OCCCC)(OCCCC)=O)CCC.[Cu]C#N.[F-].[K+]>C1(C)C=CC=CC=1>[CH2:35]([O:34][P:27]([C:5]1[CH:6]=[C:2]([C:7]2[S:8][C:9]([C:24]3[S:23][CH:22]=[CH:26][CH:25]=3)=[CH:10][CH:11]=2)[S:3][C:4]=1[C:24]1[S:23][C:22]([C:20]2[S:21][C:17]([C:20]3[S:21][CH:17]=[CH:18][CH:19]=3)=[CH:18][CH:19]=2)=[C:26]([P:27]([O:29][CH2:30][CH2:31][CH2:32][CH3:33])([O:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:28])[CH:25]=1)([O:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:28])[CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 4

HCID 522689Potassium FluorideHCID 673353012-IodobithiopheneHCID 866384215,5'-Bis(tributylstannyl)-4,3'-bis(dibutoxyphosphoryl)-[2,2']-bithiopheneHCID 178418546HCID 178418546, compound

Product 1

HCID 591559064'',4'''-Bis(dibutoxyphosphoryl)-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']-sexithiopheneYield 39%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, 0.0643 g (0.220 mmols) of 2-iodobithiophene and 0.0046 g (0.00398 mmols) of commercially available tetrakistriphenylphosphine palladium were dissolved in toluene, to which 0.113 g (0.100 mmol) of 5,5′-bis(tributylstannyl)-4,3′-bis(dibutoxyphosphoryl)-[2,2′]-bithiophene and 0.0018 g (0.020 mmols) of commercially available copper(I) cyanide were added at room temperature. Thereafter, the reaction mixture was heated and stirred under reflux for 3 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a potassium fluoride aqueous solution was added, followed by stirring for 1 hour. Subsequently, the solid was removed by celite filtration and the filtrate was extracted with ethyl acetate. The organic phase was washed with a saturate saline solution and dried over anhydrous sodium sulfate. The solvent was removed by distilling off under reduced pressure, and the resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane=1:10) to obtain the specified substance in the form of a red solid at a yield of 0.0345 g (yield: 39%).

Workup

  1. additionwere added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux for 3 hours
  4. customAfter the reaction
  5. additionwas added
  6. stirringby stirring for 1 hour
  7. customSubsequently, the solid was removed by celite filtration
  8. extractionthe filtrate was extracted with ethyl acetate
  9. washThe organic phase was washed with a saturate saline solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed
  12. distillationby distilling off under reduced pressure
  13. customthe resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane=1:10)
  14. customto obtain the specified substance in the form of a red solid at a yield of 0.0345 g (yield: 39%)

Sources & evidence

ORD record
ord-ae3144a02468468fb7c72d7de4a1d203
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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