Potassium Fluoride → 3''',4''-Bis(diethoxyphosphoryl)-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']-sexithiophene

HRID 1662883Notes

Reaction equation

HRID 1662883 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.[CH2:12]([O:14][P:15]([C:20]1[CH:24]=[C:23]([Sn](CCCC)(CCCC)CCCC)[S:22][C:21]=1[C:38]1[S:39][C:40]([Sn](CCCC)(CCCC)CCCC)=[CH:41][C:42]=1[P:43]([O:48][CH2:49][CH3:50])([O:45][CH2:46][CH3:47])=[O:44])([O:17][CH2:18][CH3:19])=[O:16])[CH3:13].[F-].[K+]>CN(C=O)C>[CH2:46]([O:45][P:43]([C:42]1[CH:41]=[C:40]([C:4]2[S:3][C:2]([C:7]3[S:8][CH:9]=[CH:10][CH:11]=3)=[CH:6][CH:5]=2)[S:39][C:38]=1[C:21]1[S:22][C:23]([C:4]2[S:3][C:2]([C:7]3[S:8][CH:9]=[CH:10][CH:11]=3)=[CH:6][CH:5]=2)=[CH:24][C:20]=1[P:15]([O:17][CH2:18][CH3:19])([O:14][CH2:12][CH3:13])=[O:16])([O:48][CH2:49][CH3:50])=[O:44])[CH3:47]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 673353012-IodobithiopheneHCID 866384163,3'-Bis(diethoxyphosphoryl)-5,5'-bis(tributylstannyl)-[2,2']-bithiophene

Product 1

HCID 591558583''',4''-Bis(diethoxyphosphoryl)-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']-sexithiopheneYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, 0.0065 g (0.0056 mmols) of commercially available tetrakistriphenylphosphine palladium and 0.0818 g (0.28 mmols) of 2-iodobithiophene were dissolved in DMF. Thereafter, 0.1345 g (0.14 mmols) of 3,3′-bis(diethoxyphosphoryl)-5,5′-bis(tributylstannyl)-[2,2′]-bithiophene was added at room temperature. The reaction mixture was heated and stirred under reflux for 5 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 2 hours. Thereafter, the solid was removed by celite filtration and the filtrate was extracted with ethyl acetate. The organic phase was washed with a saturated 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=1:5 and ethyl acetate:hexane=1:1) to obtain the specified substance in the form of a yellow solid at a yield of 0.0451 g (yield: 42%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customAfter the reaction
  4. additionwas added
  5. stirringby stirring for 2 hours
  6. customThereafter, the solid was removed by celite filtration
  7. extractionthe filtrate was extracted with ethyl acetate
  8. washThe organic phase was washed with a saturated saline solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed
  11. distillationby distilling off under reduced pressure
  12. customthe resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane=1:5 and ethyl acetate:hexane=1:1)
  13. customto obtain the specified substance in the form of a yellow solid at a yield of 0.0451 g (yield: 42%)

Sources & evidence

ORD record
ord-e90eac04276846a2bcbaa4385eb0e9d1
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

Loading…