Acetic Acid → HCID 58261091, Verbindung

HRID 2363760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2363760
[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

Komponenten

8

Edukt 4

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

Produkt 1

HCID 58261091HCID 58261091, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 23994ZincKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-de08b895710b450ba8be6b66d360cffa
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691931B2

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