Water → 2-Bromo-4-nitrobenzoic acid

HRID 356089Notes

Reaction equation

HRID 356089 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].N1C=CC=CC=1.[O-:18][Mn](=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:18])=[O:24]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 821892-Bromo-4-nitrotolueneHCID 516875Potassium Permanganate

Product 1

HCID 3135342-Bromo-4-nitrobenzoic acid

Procedure

2-bromo-4-nitrotoluene (5.00 g, 23.14 mmol) was dissolved into pyridine (23 ml) and water (46 ml). The heterogeneous mixture was heated to 60 ∞C and KMnO4 (18.29 g, 115.7 mmol) was added carefully. The mixture was then heated under reflux overnight. The reaction mixture was filtered and washed with boiling water. The solution was then made acidic and extracted into ethyl acetate, dried over Na2SO4, and the solvent was removed in vacuo. A crude NMR revealed remaining starting material so the solid was taken up in NaOH and washed with hexanes. The aqueous phase was made acidic and the product was extracted into ethyl acetate. The ethyl acetate fractions were combined and dried over Na2SO4 and the solvent was removed in vacuo to yield 3.72 g (65.4%). mp 158°-160C.; 1H NMR (CD3OD) 7.81 (1 H, d, J=8.5 Hz), 8.08 (1 H, d, J=8.5 Hz), 8.30 (1 H, s); 13C NMR (CD3OD) 121.96, 122.75, 129.36, 132.24, 139.52, 149.54, 167.75; anal. calc. for C7H4BrNO4 +0.1 ethyl acetate, C: 34.88, H: 1.90, N: 5.50; found, C: 34.68, H: 1.86, N: 5.82.

Workup

  1. additionwas added carefully
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux overnight
  4. filtrationThe reaction mixture was filtered
  5. washwashed with boiling water
  6. extractionmade acidic and extracted into ethyl acetate
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed in vacuo
  9. washwashed with hexanes
  10. extractionthe product was extracted into ethyl acetate
  11. dry with materialdried over Na2SO4
  12. customthe solvent was removed in vacuo
  13. customto yield 3.72 g (65.4%)

Sources & evidence

ORD record
ord-a405645a4b794253922215f77dc37555
Source dataset
uspto-grants-1998_11
Patent number
US05834434

Reaction notes

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