Acetic Acid → HCID 58261091, compound

HRID 2363760Notes

Reaction equation

HRID 2363760 reaction equation
[Br:1][C:2]1[S:3][C:4](Br)=[C:5]2[C:9](=[O:10])[N:8]([CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])[C:7](=[O:19])[C:6]=12.C(O)C.C(O)(=O)C.CCCCCC>Cl.[Zn].C(Cl)(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[C:5]2[C:9](=[O:10])[N:8]([CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])[C:7](=[O:19])[C:6]=12

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 8058HexaneHCID 582610781,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Product 1

HCID 58261091HCID 58261091, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23994ZincCatalystHCID 6212ChloroformSolvent

Procedure

1,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (2.6 g, 5 mmol) was placed in a three neck round-bottom flask equipped with a water condenser with ethanol (35 mL), acetic acid (10 mL) and three drops of 1 M HCl. The mixture was heated until the starting material was fully dissolved. At this point, zinc (310 mg, 5 mmol) was added in one portion. Mixture was refluxed for one hour after which an aliquot was taken for GC analysis and NMR, indicating reaction completion. After cooling, the solution was filtered through fitted glass to eliminate remaining Zn particles and solvent was evaporated under vacuum. Product was obtained by silica chromatography (1.1 g, 52%), using a 100% hexane to 100% CHCl3 gradient.

Workup

  1. temperatureThe mixture was heated until the starting material
  2. dissolutionwas fully dissolved
  3. temperatureMixture was refluxed for one hour after which an aliquot
  4. customreaction completion
  5. temperatureAfter cooling
  6. filtrationthe solution was filtered
  7. customthrough fitted glass
  8. customwas evaporated under vacuum
  9. customProduct was obtained by silica chromatography (1.1 g, 52%)

Sources & evidence

ORD record
ord-de08b895710b450ba8be6b66d360cffa
Source dataset
uspto-grants-2014_04
Patent number
US08691931B2

Reaction notes

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