Acetic Acid → 1,4-Naphthalenedione, 2-bromo-8-hydroxy-

HRID 2369452Notes

Reaction equation

HRID 2369452 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:13])[CH:5]=[CH:6][C:7]2=[O:12].[Br:14]Br.C(O)(=O)C.C(O)C>C(Cl)(Cl)Cl>[CH:10]1[CH:11]=[C:2]([OH:1])[C:3]2[C:4]([C:5]([Br:14])=[CH:6][C:7](=[O:12])[C:8]=2[CH:9]=1)=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 3806JugloneHCID 24408Bromine

Product 1

HCID 9275141,4-Naphthalenedione, 2-bromo-8-hydroxy-Yield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-hydroxynaphthalene-1,4-dione (171 mg, 1 mmol) in chloroform was added bromine, and the mixture was stirred. Then, to the resulting mixture were added acetic acid and ethanol, and the mixture was stirred under reflux to give 3-bromojuglone (80%). To the resulting 3-bromojuglone was added dimethylamine, and the mixture was stirred in toluene at room temperature to give 2-dimethylaminojuglone and 3-dimethylaminojuglone (85%).

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux

Sources & evidence

ORD record
ord-24342e7789db449b9224f6c44d03df21
Source dataset
uspto-grants-2014_04
Patent number
US08703979B2

Reaction notes

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