O-Phenylenediamine → 2,3-Bis(4-bromophenyl)quinoxaline

HRID 888702Notes

Reaction equation

HRID 888702 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)=O)=O)=[CH:4][CH:3]=1.[C:19]1([NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:25]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:10]([C:12]3[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=3)=[N:26][C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:25]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 964304,4'-Dibromobenzil

Product 1

HCID 5549772,3-Bis(4-bromophenyl)quinoxalineYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

30.2 g of 4,4′-dibromobenzil (82.0 mmol), 9.31 g of 1,2-phenylenediamine (86.1 mmol), and 300 mL of chloroform were put into a 500 mL three-necked flask. This reaction solution was refluxed for five hours at 80° C. under a nitrogen gas stream. After the reaction, the reaction solution was cooled to room temperature and washed with water. A water layer was extracted with chloroform, the extracted solution and an organic layer were dried by magnesium sulphate. After drying, the mixture was filtrated by suction to concentrate the filtrate. The obtained solid was dissolved in toluene and this solution was filtrated by suction through Florisil, celite, and alumina. The filtrate was condensed, and 30 g of an objective matter, a white powder solid, 2,3-bis(4-bromophenyl)quinoxaline was obtained at the yield 99%.

Workup

  1. customAfter the reaction
  2. temperaturethe reaction solution was cooled to room temperature
  3. washwashed with water
  4. extractionA water layer was extracted with chloroform
  5. dry with materialthe extracted solution and an organic layer were dried by magnesium sulphate
  6. customAfter drying
  7. filtrationthe mixture was filtrated by suction
  8. concentrationto concentrate the filtrate
  9. dissolutionThe obtained solid was dissolved in toluene
  10. filtrationthis solution was filtrated by suction through Florisil, celite, and alumina
  11. customcondensed, and 30 g of an objective matter

Sources & evidence

ORD record
ord-02b5a0b701224521acc46da9f429bb1e
Source dataset
uspto-grants-2012_08
Patent number
US08252433B2

Reaction notes

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