Hydrochloric Acid → 3'',4''-Bis(diethoxyphosphoryl)-[2,2';5',2'';5'',2''';5''',2'''']-quinquethiophene

HRID 1662874Notes

Reaction equation

HRID 1662874 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][C:8]([Sn](CCCC)(CCCC)CCCC)=[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.[Cu]C#N.I[C:52]1([C:57]2[S:58][CH:59]=[CH:60][CH:61]=2)[CH2:56][CH:55]=[CH:54][S:53]1.Cl>>[CH2:22]([O:21][P:19]([C:9]1[C:10]([P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([C:54]2[S:53][C:52]([C:57]3[S:58][CH:59]=[CH:60][CH:61]=3)=[CH:56][CH:55]=2)[S:7][C:8]=1[C:54]1[S:53][C:52]([C:57]2[S:58][CH:59]=[CH:60][CH:61]=2)=[CH:56][CH:55]=1)([O:24][CH2:25][CH3:26])=[O:20])[CH3:23]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 673353012-IodobithiopheneHCID 86638412HCID 86638412, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 591559243'',4''-Bis(diethoxyphosphoryl)-[2,2';5',2'';5'',2''';5''',2'''']-quinquethiophene

Conditions

Temperature
70 °C

Procedure

2,5-bis(tributylstannyl)-3,4-bis(diethoxyphosphoryl)-thiophene and commercially available copper(I) cyanide (2.2 equivalents) were dissolved in solvents indicated in the following Table 11, to which 2-iodobithiophene (2.2 equivalents) was added at room temperature. Thereafter, the reaction mixture was heated to 70° C. and stirred for 4 to 22 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a 0.6M hydrochloric acid aqueous solution was added, followed by extraction of the resulting product 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 product was purified with a silica gel column (ethyl acetate:methanol=15:1) to obtain the specified substance 1.

Workup

  1. additionwas added at room temperature
  2. customAfter the reaction
  3. additionwas added
  4. extractionfollowed by extraction of the resulting product with ethyl acetate
  5. washThe organic phase was washed with a saturated saline solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. distillationby distilling off under reduced pressure
  9. customthe resulting product was purified with a silica gel column (ethyl acetate:methanol=15:1)
  10. customto obtain the specified substance 1

Sources & evidence

ORD record
ord-31d77bd87f2248d6bc5dd07178706b43
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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