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

HRID 2193974Notes

Reaction equation

HRID 2193974 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 6057498,9-Dihydrocyclopenta[def]phenanthreneYield 147.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

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%).

Workup

  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 (mobile solvent: n-hexane)

Sources & evidence

ORD record
ord-72298c4e8f644ac1956ef2e6d1d92123
Source dataset
uspto-grants-2012_12
Patent number
US08329953B2

Reaction notes

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