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

HRID 254129

Reaction equation

HRID 254129 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]=[CH:9][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 125243632-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

Product 1

HCID 6057498,9-Dihydrocyclopenta[def]phenanthreneYield 111%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

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%).

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 (developing solvent: n-hexane)

Sources & evidence

ORD record
ord-3ecb0238b0f745b2b0fe412e878b5c3c
Source dataset
uspto-grants-2011_01
Patent number
US07875367B2

Linked notes

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