2-Iodothiophene → HCID 86638406, compound

HRID 1662864Notes

Reaction equation

HRID 1662864 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[C:9]([P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])[C:10]=1[P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])CCC.I[C:36]1[S:37][CH:38]=[CH:39][CH:40]=1.[F-].[K+]>C1COCC1.[Cu]Cl>[CH2:14]([O:13][P:11]([C:10]1[C:9]([P:19]([O:21][CH2:22][CH3:23])([O:24][CH2:25][CH3:26])=[O:20])=[CH:8][S:7][C:6]=1[C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)([O:16][CH2:17][CH3:18])=[O:12])[CH3:15]

Participants

6

Reactant 3

HCID 189212-IodothiopheneHCID 522689Potassium FluorideHCID 86638407HCID 86638407, compound

Product 1

HCID 86638406HCID 86638406, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In THF, 0.600 g (0.930 mmols) of 2-tributylstannyl-3,4-bis(diethoxyphosphoryl)thiophene and 0.1013 g (1.023 mmols) of commercially available copper(I) chloride were dissolved, to which 0.2344 g (1.116 mmols) of 2-iodothiophene was added at room temperature. Thereafter, the reaction mixture was heated and stirred under reflux for 4 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. Subsequently, the resulting 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 (ethyl acetate:methanol=15:1) to obtain the specified substance at a yield of 0.3595 g (yield: 88%).

Workup

  1. additionwas added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux for 4 hours
  4. customAfter the reaction
  5. additionwas added
  6. stirringby stirring for 2 hours
  7. customSubsequently, the resulting 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 (ethyl acetate:methanol=15:1)
  14. customto obtain the specified substance at a yield of 0.3595 g (yield: 88%)

Sources & evidence

ORD record
ord-f74980e157ff4234aa33c1f33034aad5
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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