Reaktion #341311

Reaktionsgleichung

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

o-chloranil

→

compound 1

Ausbeute 111.0%

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

Ausbeute 111.0%

Lösungsmittel

xylene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigeat room temperature
3. 3
   TemperaturThe reaction mixture was heated
4. 4
   Temperaturrefluxed in an oil bath for 72 hours
5. 5
   SonstigeAfter the reaction was terminated
6. 6
   Temperaturthe reaction solution was cooled
7. 7
   Einengenconcentrated under a reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (developing solvent: n-hexane)

Vorschrift

2-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene (4.45 g, 16.4 mmol) in a 250 ml round bottom flask was dissolved with xylene, and o-chloranil (4.3 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 (developing solvent: n-hexane) to give a compound 1 (3.5 g, 79%).

Quelle