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

HRID 2075420Notes

Reaction equation

HRID 2075420 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-2a747f9f496648d093f44b1f189012b6
Source dataset
uspto-grants-2011_04
Patent number
US07919654B2

Reaction notes

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