Sodium Iodide → HCID 59426893, compound

HRID 557689Notes

Reaction equation

HRID 557689 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]([CH:18]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:19]Br)[CH3:17]>CS(C)=O.O>[CH2:16]([CH:18]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:19][C:6]1([CH2:6][CH:3]([CH2:4][CH3:5])[CH2:2][CH2:8][CH2:7][CH3:11])[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)[CH3:17]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 14797Potassium HydroxideHCID 868042-Ethylhexyl bromideHCID 1362324H-Cyclopenta(2,1-b:3,4-b')dithiophene

Product 1

HCID 59426893HCID 59426893, compound

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). After the solution was purged with nitrogen, and grounded KOH (1.89 g, 0.0337 mol), sodium iodide (50 mg), and 2-ethylhexyl bromide (3.25 g, 0.0169 mol) were sequentially added. The reaction mixture was stirred overnight under nitrogen (c.a. 16 hours). Water was added and the reaction was extracted with t-butylmethyl ether. The organic layer was collected, dried over magnesium sulfate, and concentrated. The residue was purified by chromatography using hexanes as eluent. Fractions containing pure 4,4-Bis-(2-ethyl-hexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene product were combined and concentrated. The product was obtained as a colorless oil after drying under vacuum. Yield: 2.68 g (79%). 1H NMR (CDCl3, 250 MHz): 7.13 (m, 2H), 6.94 (m, 2H), 1.88 (m, 4H), 0.94 (m, 16H), 0.78 (t, 6.4 Hz, 6H), 0.61 (t, 7.3 Hz, 6H).

Workup

  1. customAfter the solution was purged with nitrogen
  2. additionwere sequentially added
  3. extractionthe reaction was extracted with t-butylmethyl ether
  4. customThe organic layer was collected
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography
  8. additionFractions containing pure 4,4-Bis-(2-ethyl-hexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene product
  9. concentrationconcentrated
  10. customThe product was obtained as a colorless oil
  11. customafter drying under vacuum

Sources & evidence

ORD record
ord-63e59fa22e284511ba7f0078f4dbf10b
Source dataset
uspto-grants-2011_11
Patent number
US08058550B2

Reaction notes

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