o-Chloranil → 8,9-Dihydrocyclopenta[def]phenanthrene

HRID 1172019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172019
Br[C:2]1[CH:15]=[C:14]2[CH2:16][C:11]3[C:12]4[C:13]2=[C:4]([CH2:5][CH2:6][C:7]=4[CH:8]=[C:9](Br)[CH:10]=3)[CH:3]=1.C1(Cl)C(Cl)=C(Cl)C(=O)C(=O)C=1Cl>C1(C)C(C)=CC=CC=1>[CH:3]1[C:4]2[CH2:5][CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[CH2:16][C:14]([C:13]=2[C:12]=34)=[CH:15][CH:2]=1

Komponenten

4

Edukt 2

HCID 73252o-ChloranilHCID 125243672,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

Produkt 1

HCID 6057498,9-Dihydrocyclopenta[def]phenanthreneAusbeute 147,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

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 (developing solvent: n-hexane) to give a compound 1 (3.6 g, 81%).

Aufarbeitung

  1. additionwas added
  2. customat room temperature
  3. temperatureThe reaction mixture was heated
  4. temperaturerefluxed in an oil bath for 72 hours
  5. customAfter the reaction was terminated
  6. temperaturethe reaction solution was cooled
  7. concentrationconcentrated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (developing solvent: n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e49e7b12a83f426287d6fa7ee482972a
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833635B2

Notizen zur Reaktion

Wird geladen…