6-Bromo-8-(2-ethylhexoxy)-4-(2-ethylhexyl)thieno[2,3-f]benzothiophene → 4-(2-Ethylhexoxy)-8-(2-ethylhexyl)thieno[2,3-f]benzothiophene-2-carbonitrile

HRID 2363759Notes

Reaction equation

HRID 2363759 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])=[C:9]3[CH:19]=[CH:20][S:21][C:8]3=[C:7]([O:22][CH2:23][CH:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])[C:5]=2[CH:6]=1.[Cu][C:32]#[N:33]>>[CH2:29]([CH:24]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23][O:22][C:7]1[C:8]2[S:21][CH:20]=[CH:19][C:9]=2[C:10]([CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])=[C:4]2[S:3][C:2]([C:32]#[N:33])=[CH:6][C:5]=12)[CH3:30]

Participants

3

Reactant 2

HCID 582610906-Bromo-8-(2-ethylhexoxy)-4-(2-ethylhexyl)thieno[2,3-f]benzothiopheneHCID 178418546HCID 178418546, compound

Product 1

HCID 582610964-(2-Ethylhexoxy)-8-(2-ethylhexyl)thieno[2,3-f]benzothiophene-2-carbonitrileYield 38%

Procedure

A dry 100-mL three-neck flask, equipped with a condenser, charged with 6-bromo-8-(2-ethylhexoxy)-4-(2-ethylhexyl)thieno[2,3-f]benzothiophene (4.2 g, 8.2 mmol) and flushed with N2. Deoxygenated pyridine (15 mL, 0.5 M) was then added via syringe. Copper (I) cyanide (2.2 g, 25 mmol) was added to the reaction flask and the mixture was evacuated and refilled with nitrogen three times. The reaction flask was heated to reflux for 48 hours. As the reaction was completed, the reaction mixture was poured into 50 mL of water and extracted with MTBE (50 mL) three times. The combined organic layer was washed with water two times and dried over anhydrous magnesium sulfate (MgSO4). After the product was filtered, the solvent was removed by rotary evaporation. The product was purified using column chromatography on silica gel with hexanes/ethyl acetate (gradient) to yield oil (1.4 g, 38%).

Workup

  1. customA dry 100-mL three-neck flask, equipped with a condenser
  2. customflushed with N2
  3. additionDeoxygenated pyridine (15 mL, 0.5 M) was then added via syringe
  4. customthe mixture was evacuated
  5. additionrefilled with nitrogen three times
  6. temperatureThe reaction flask was heated
  7. temperatureto reflux for 48 hours
  8. additionthe reaction mixture was poured into 50 mL of water
  9. extractionextracted with MTBE (50 mL) three times
  10. washThe combined organic layer was washed with water two times
  11. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  12. filtrationAfter the product was filtered
  13. customthe solvent was removed by rotary evaporation
  14. customThe product was purified

Sources & evidence

ORD record
ord-dcb437a660214688a5fe089174350f96
Source dataset
uspto-grants-2014_04
Patent number
US08691931B2

Reaction notes

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