Réaction #593026

Équation de réaction

2,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

o-chloranil

→

compound 1

Rendement 147.4%

8,9-dihydro-4H-cyclopenta[def]phenanthrene

Rendement 147.4%

Solvants

xylene

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   Autreat room temperature
3. 3
   TempératureThe reaction mixture was heated
4. 4
   Températurerefluxed in an oil bath for 72 hours
5. 5
   AutreAfter the reaction was terminated
6. 6
   Températurethe reaction solution was cooled
7. 7
   Concentrationconcentrated under a reduced pressure
8. 8
   AutreThe residue was purified by silica gel column chromatography (mobile solvent: n-hexane)

Mode opératoire

2,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene (4.45 g, 12.7 mmol) in a 250 ml round bottom flask was dissolved with xylene, and o-chloranil (4.15 g) was added thereto at room temperature. The reaction mixture was heated and refluxed in an oil bath for 72 hours. After the reaction was terminated, the reaction solution was cooled and concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (mobile solvent: n-hexane) to give a compound 1 (3.6 g, 81%).

Source