2,5-Dibromohydroquinone → 2,5-Dibromo-1,4-benzoquinone

HRID 1060618Notes

Reaction equation

HRID 1060618 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([OH:9])[C:6]([Br:10])=[CH:5][C:3]=1[OH:4].[N+]([O-])([O-])=O.[NH4+].[Ce]>C(#N)C.O>[Br:1][C:2]1[C:3](=[O:4])[CH:5]=[C:6]([Br:10])[C:7](=[O:9])[CH:8]=1

Participants

5

Reactant 2

HCID 2809452,5-DibromohydroquinoneHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 5430932,5-Dibromo-1,4-benzoquinoneYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,5-dibromohydroquinone (1) (5 g, 18.6 mol) in acetonitrile (250 ml) was added cerium ammonium nitrate (21.4 g, 39.0 mmol), in small portions. The clear orange solution was stirred for 10 min at room temperature, diluted with water (80 ml) and extracted with chloroform (3×200 ml). The combined chloroform layers were dried over sodium sulphate and evaporated, yielding 3.5 g (71%) of the quinone (2).

Workup

  1. extractionextracted with chloroform (3×200 ml)
  2. dry with materialThe combined chloroform layers were dried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-58327378666747f79ea504e3e98fc7d5
Source dataset
uspto-grants-2003_02
Patent number
US06525063B2

Reaction notes

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