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

HRID 1662875Notes

Reaction equation

HRID 1662875 reaction equation
I[C:2]1[S:3][C:4](I)=[C:5]([P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])[C:6]=1[P:7]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])=[O:8].C([Sn]([C:37]1[CH:41]=[CH:40][S:39][C:38]=1[C:42]1[S:43][CH:44]=[CH:45][CH:46]=1)(CCCC)CCCC)CCC.Cl>CN(C=O)C.[Cu]Cl>[CH2:10]([O:9][P:7]([C:6]1[C:5]([P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])=[C:4]([C:40]2[S:39][C:38]([C:42]3[S:43][CH:44]=[CH:45][CH:46]=3)=[CH:37][CH:41]=2)[S:3][C:2]=1[C:44]1[S:43][C:42]([C:38]2[S:39][CH:40]=[CH:41][CH:37]=2)=[CH:46][CH:45]=1)([O:12][CH2:13][CH3:14])=[O:8])[CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 22634623TributylstannylbithiopheneHCID 866384112,5-Diiodo-3,4-bis(diethoxyphosphoryl)thiophene

Product 1

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

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In DMF, 0.0971 g (0.159 mmols) of 2,5-diiodo-3,4-bis(diethoxyphosphoryl)thiophene and 0.0346 g (0.349 mmols) of commercially available copper(I) chloride were dissolved, to which 0.1744 g (0.383 mmols) of tributylstannylbithiophene was added at room temperature. Thereafter, the reaction mixture was heated to 80° C. and stirred for 12 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a 0.6 M 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. The results are shown in Table 12.

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-55830777472b4bd393e61b4135d7380c
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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