Sodium Iodide → 4,4-Dihexyl-4H-cyclopenta[1,2-b:5,4-b']bisthiophene

HRID 506142Notes

Reaction equation

HRID 506142 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH2:6][C:7]3[CH:11]=[CH:10][S:9][C:8]=3[C:2]1=2.[OH-].[K+].[I-].[Na+].[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CS(C)=O.O>[CH2:16]([C:6]1([CH2:7][CH2:8][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]2[CH:11]=[CH:10][S:9][C:8]=2[C:2]2[S:1][CH:5]=[CH:4][C:3]1=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81011-BromohexaneHCID 14797Potassium HydroxideHCID 1362324H-Cyclopenta(2,1-b:3,4-b')dithiophene

Product 1

HCID 594268924,4-Dihexyl-4H-cyclopenta[1,2-b:5,4-b']bisthiophene

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

4H-Cyclopenta[2,1-b;3,4-b′]dithiophene (1.5 g, 0.00843 mol) was dissolved in DMSO (50 mL). The solution was purged with nitrogen, and grounded KOH (1.89 g, 0.0337 mol) and sodium iodide (50 mg) were added, followed by hexyl bromide (3.02 g, 0.0169 mol). The reaction was stirred for 17 h under nitrogen at room temperature. Water was added and the reaction was extracted with t-butyl-methyl ether. The organic layer was separated and dried over magnesium sulfate. Solvent was removed under vacuum and the residue was purified by chromatography using hexanes as eluent. Fractions containing pure 4,4-dixeyl-4H-cyclopenta[2,1-b;3,4-b′]dithiophene product were combined and the solvents evaporated. The product was obtained as a colorless oil. Yield: 2.36 g (81%).

Workup

  1. customThe solution was purged with nitrogen
  2. additionwere added
  3. extractionthe reaction was extracted with t-butyl-methyl ether
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customSolvent was removed under vacuum
  7. customthe residue was purified by chromatography
  8. additionFractions containing pure 4,4-dixeyl-4H-cyclopenta[2,1-b;3,4-b′]dithiophene product
  9. customthe solvents evaporated
  10. customThe product was obtained as a colorless oil

Sources & evidence

ORD record
ord-b2b16aab3e224f12b65ad93f507ad166
Source dataset
uspto-grants-2010_08
Patent number
US07781673B2

Reaction notes

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