Réaction #955963

Équation de réaction

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

Solvants

CHCl3

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source