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

HRID 1878047
Notes
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Reaction equation

HRID 1878047 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140Toluene
Solvent

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, which were refluxed under nitrogen stream at 80° C. for 5 hours. After a predetermined time, the solution was cooled to room temperature, and there was added water. The aqueous layer was extracted with chloroform, and the extract and the organic layer were dried together over magnesium sulfate. After drying, the mixture was subjected to suction filtration, and the filtrate was condensed. The obtained solid was dissolved in toluene, and the 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 condensed; thus, 30 g of target white powder of 2,3-bis(4-bromophenyl)quinoxaline was obtained with a yield of 99%.

Workup

  1. customIn a 500 mL three-necked flask were placed
  2. extractionThe aqueous layer was extracted with chloroform
  3. extractionthe extract
  4. dry with materialthe organic layer were dried together over magnesium sulfate
  5. customAfter drying
  6. filtrationthe mixture was subjected to suction filtration
  7. customcondensed
  8. filtrationthe 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. customcondensed

Sources & evidence

ORD record
ord-c291355bb9c14e79b2aa718e3d703db0
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08314101B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes