Toluene → HCID 59155936, compound

HRID 1662895Notes

Reaction equation

HRID 1662895 reaction equation
I[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([O:11][P:12]([C:19]1[CH:20]=[C:21]([C:37]2[S:38][C:39]([Sn](CCCC)(CCCC)CCCC)=[C:40]([P:42]([O:49][CH2:50][CH2:51][CH2:52][CH3:53])([O:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:43])[CH:41]=2)[S:22][C:23]=1[Sn:24]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29]CCC)[CH2:25][CH2:26][CH2:27][CH3:28])([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])[CH2:8][CH2:9][CH3:10].[F-].[K+].[C:69]1(C)[CH:74]=CC=C[CH:70]=1>>[CH2:45]([O:44][P:42]([C:40]1[CH:41]=[C:37]([C:21]2[S:22][C:23]([Sn:24]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:29][CH2:70][CH2:69][CH3:74])=[C:19]([P:12]([O:11][CH2:7][CH2:8][CH2:9][CH3:10])([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])[CH:20]=2)[S:38][C:39]=1[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1)([O:49][CH2:50][CH2:51][CH2:52][CH3:53])=[O:43])[CH2:46][CH2:47][CH3:48]

Participants

5

Reactant 4

HCID 1140TolueneHCID 189212-IodothiopheneHCID 522689Potassium FluorideHCID 59155963HCID 59155963, compound

Product 1

HCID 59155936HCID 59155936, compoundYield 53%

Procedure

At room temperature, 0.1285 g (0.44 mmols) of 2-iodothiophene and 0.0092 g (0.008 mmols) of commercially available tetrakistriphenylphosphine palladium were dissolved in toluene, to which 0.1961 g (0.200 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. 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 silica gel column to obtain the specified substance in the form of a red solid at a yield of 0.0634 g (yield: 53%). The thus obtained substance was used as it is for reaction in Example 12(26).

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. customThereafter, the solid was removed by celite filtration
  8. extractionthe filtrate was extracted with ethyl acetate
  9. washThe organic phase was washed with a saturated 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 silica gel column
  14. customto obtain the specified substance in the form of a red solid at a yield of 0.0634 g (yield: 53%)
  15. customis for reaction in Example 12(26)

Sources & evidence

ORD record
ord-3cf04a3d3f7c40238a11fda50cd9736d
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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