Water → 2-Bromo-4-nitrobenzoic acid

HRID 1068867Notes

Reaction equation

HRID 1068867 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].S([O-])(O)(=O)=[O:13].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].[OH2:24]>>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([OH:13])=[O:24]

Participants

5

Reactant 4

HCID 962WaterHCID 821892-Bromo-4-nitrotolueneHCID 516875Potassium PermanganateHCID 516919Sodium Bisulfate

Product 1

HCID 3135342-Bromo-4-nitrobenzoic acidYield 53%

Procedure

75 g (0.35 mol) of 2-bromo-4-nitrotoluene, 12 ml of aliquot 336 and 39 g (0.47 mol) of sodium hydrogen sulfate in 1.5 l of water were heated to 80° C. The mixture was stirred well and 183 g (1.16 mol) of potassium permanganate were then added a little at a time. The mixture was then heated under reflux for 45 min. The mixture was filtered through CELITE and the filtrate was concentrated to about 700 ml under reduced pressure. The aqueous solution was acidified with concentrated hydrochloric acid, whereupon the product precipitated. 45 g (53%) of the product were obtained.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 45 min
  3. filtrationThe mixture was filtered through CELITE
  4. concentrationthe filtrate was concentrated to about 700 ml under reduced pressure
  5. customprecipitated

Sources & evidence

ORD record
ord-40bc3c98341143ffaefaf2ba2b5ac0f2
Source dataset
uspto-grants-2001_06
Patent number
US06251917B1

Reaction notes

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