2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2,7-Dibromophenanthrene

HRID 751744

Reaction equation

HRID 751744 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[CH2:6][CH2:5][C:4]=2[CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 28250532,7-Dibromo-9,10-dihydrophenanthrene

Product 1

HCID 111750732,7-DibromophenanthreneYield 47.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Preparing 32.7 g of 2,7-dibromo-9,10-dihydrophenanthrene, 24.1 g of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) and 500 milliliter of benzene as a mixture solution, the solution was refluxed with heating under an ambient atmosphere of argon gas for 64 hours. The reacted solution was cooled down to a room temperature, and further filtered. Concentrating the filtrate by means of an evaporator, the residue was washed with a use of methanol. After refining the filtered product by means of a short column, the refined product was re-crystallized with a use of toluene and as a result, 15.5 g of 2,7-dibromophenanthrene was obtained as colorless needle crystals.

Workup

  1. temperaturethe solution was refluxed
  2. temperaturewith heating under an ambient atmosphere of argon gas for 64 hours
  3. concentrationConcentrating the filtrate
  4. customby means of an evaporator
  5. washthe residue was washed with a use of methanol
  6. customthe refined product was re-crystallized with a use of toluene and as a result

Sources & evidence

ORD record
ord-56df3de2a9824db3b0fe2b1e3dc6b3ed
Source dataset
uspto-grants-2008_07
Patent number
US07405326B2

Linked notes

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