Reaktion #955963

Reaktionsgleichung

ethanol

acetic acid

hexane

1,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

→

1-bromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated until the starting material
2. 2
   workup.DISSOLUTIONwas fully dissolved
3. 3
   TemperaturMixture was refluxed for one hour after which an aliquot
4. 4
   Sonstigereaction completion
5. 5
   TemperaturAfter cooling
6. 6
   Filtrationthe solution was filtered through fritted glass
7. 7
   Sonstigewas evaporated under vacuum
8. 8
   SonstigeProduct was obtained by silica chromatography (1.1 g, 52%)

Vorschrift

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 fritted 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.

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