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

HRID 553374Notes

Reaction equation

HRID 553374 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 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A chloroform solution (200 mL) of 30.0 g (81.5 mmol) of 4,4′-dibromobenzil and 9.00 g (83.2 mmol) of o-phenylenediamine was heated and refluxed at 80° C. for 3 hours under nitrogen atmosphere. The reaction solution was washed with water after being cooled to room temperature. An aqueous layer was extracted with chloroform. This extracted aqueous layer and an organic layer were put together and washed with a saturated saline solution. The organic layer was dried over magnesium sulfate and filtered. The filtrate was condensed to obtain 33 g (yield: 92%) of objective 2,3-bis(4-bromophenyl)quinoxaline as a white solid. Synthetic scheme of Step 1 is shown in the following (d-1).

Workup

  1. washThe reaction solution was washed with water
  2. temperatureafter being cooled to room temperature
  3. extractionAn aqueous layer was extracted with chloroform
  4. washwashed with a saturated saline solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customcondensed

Sources & evidence

ORD record
ord-fa8f6dad7ad047a4b8e62d003cb4b1e2
Source dataset
uspto-grants-2011_11
Patent number
US08048540B2

Reaction notes

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