Chloroform → 2,3-Bis(4-bromophenyl)quinoxaline

HRID 2076739Notes

Reaction equation

HRID 2076739 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>O>[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

5

Reactant 3

HCID 6212ChloroformHCID 7243O-PhenylenediamineHCID 964304,4'-Dibromobenzil

Product 1

HCID 5549772,3-Bis(4-bromophenyl)quinoxaline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a 500 mL three-necked flask were placed 30 g (82 mmol) of 4,4′-dibromobenzil, 9.3 g (86 mmol) of 1,2-phenylenediamine, and 300 mL of chloroform. This solution was refluxed at 80° C. for 5 hours under a stream of nitrogen. After a predetermined time, the solution was cooled to room temperature, and water was added thereto. This aqueous layer was extracted with chloroform, and the extracted solution was combined with the organic layer and then dried with magnesium sulfate. After drying, the mixture was subjected to suction filtration and the filtrate was concentrated. The obtained solid was dissolved in toluene, and this solution was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) and alumina. The filtrate was concentrated, and 30 g of a white powder of 2,3-bis(4-bromophenyl)quinoxaline, which was a target substance, was obtained at a yield of 99%.

Workup

  1. customIn a 500 mL three-necked flask were placed
  2. temperatureAfter a predetermined time, the solution was cooled to room temperature
  3. extractionThis aqueous layer was extracted with chloroform
  4. dry with materialdried with magnesium sulfate
  5. customAfter drying
  6. filtrationthe mixture was subjected to suction filtration
  7. concentrationthe filtrate was concentrated
  8. dissolutionThe obtained solid was dissolved in toluene
  9. filtrationthis solution was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) and alumina
  10. concentrationThe filtrate was concentrated
  11. customwas obtained at a yield of 99%

Sources & evidence

ORD record
ord-7a911c605e2945a8b0204a6fe3f8c4c5
Source dataset
uspto-grants-2011_04
Patent number
US07927720B2

Reaction notes

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