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

HRID 2408219Notes

Reaction equation

HRID 2408219 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>C1(C)C=CC=CC=1>[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

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 7243O-PhenylenediamineHCID 964304,4'-Dibromobenzil

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a 500-mL three-neck 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 nitrogen stream. After a predetermined time, the solution was cooled to room temperature, and then, water was added thereto. The aqueous phase was extracted with chloroform, and the extracted solution combined with the organic phase was dried with magnesium sulfate. After the drying, the mixture was subjected to suction filtration and the filtrate was concentrated to give a solid. 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; thus, 30 g of a white powder of 2,3-bis(4-bromophenyl)quinoxaline, which was a product, was obtained in a yield of 99%.

Workup

  1. customIn a 500-mL three-neck flask were placed
  2. temperatureAfter a predetermined time, the solution was cooled to room temperature
  3. extractionThe aqueous phase was extracted with chloroform
  4. dry with materialwas dried with magnesium sulfate
  5. filtrationAfter the drying, the mixture was subjected to suction filtration
  6. concentrationthe filtrate was concentrated
  7. customto give a solid
  8. 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
  9. concentrationThe filtrate was concentrated
  10. customwas obtained in a yield of 99%

Sources & evidence

ORD record
ord-44cbd7bf81cf4d77b8a863b9ff2f0af4
Source dataset
uspto-grants-2014_08
Patent number
US08815412B2

Reaction notes

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