Potassium Fluoride → HCID 59155962, compound

HRID 1662893Notes

Reaction equation

HRID 1662893 reaction equation
I[C:2]1([C:7]2[S:8][CH:9]=[CH:10][C:11]=2C2SC=CC=2)[CH2:6][CH:5]=[CH:4][S:3]1.[CH2:17]([O:21][P:22]([C:29]1[CH:30]=[C:31]([C:47]2[S:48][C:49]([Sn](CCCC)(CCCC)CCCC)=[C:50]([P:52]([O:59][CH2:60][CH2:61][CH2:62][CH3:63])([O:54][CH2:55][CH2:56][CH2:57][CH3:58])=[O:53])[CH:51]=2)[S:32][C:33]=1[Sn](CCCC)(CCCC)CCCC)([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])[CH2:18][CH2:19][CH3:20].[F-].[K+]>C1(C)C=CC=CC=1>[CH2:55]([O:54][P:52]([C:50]1[CH:51]=[C:47]([C:31]2[S:32][C:33]([C:9]3[S:8][C:7]([C:2]4[S:3][C:4]([C:2]5[S:3][CH:4]=[CH:5][CH:6]=5)=[CH:5][CH:6]=4)=[CH:11][CH:10]=3)=[C:29]([P:22]([O:21][CH2:17][CH2:18][CH2:19][CH3:20])([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])[CH:30]=2)[S:48][C:49]=1[C:7]1[S:8][C:9]([C:9]2[S:8][C:7]([C:2]3[S:3][CH:4]=[CH:5][CH:6]=3)=[CH:11][CH:10]=2)=[CH:10][CH:11]=1)([O:59][CH2:60][CH2:61][CH2:62][CH3:63])=[O:53])[CH2:56][CH2:57][CH3:58]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 59155963HCID 59155963, compoundHCID 67427462HCID 67427462, compound

Product 1

HCID 59155962HCID 59155962, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, 0.1235 g (0.33 mmols) of 2-iodoterthiophene and 0.0069 g (0.006 mmols) of commercially available tetrakistriphenylphosphine palladium were dissolved in 2 ml of toluene, to which 0.1693 g (0.15 mmols) of 4,4′-bis(dibutoxyphosphoryl)-5,5′-bis(tributylstannyl)-[2,2′]-bithiophene was added at room temperature. Thereafter, the reaction mixture was heated and stirred under reflux for 2 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 0.1143 g (yield: 73%).

Workup

  1. additionwas added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux for 2 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 0.1143 g (yield: 73%)

Sources & evidence

ORD record
ord-c077f2801fd048b396fb227703dee0ce
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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