Water → 2-Bromo-4-nitrobenzoic acid

HRID 1532819Notes

Reaction equation

HRID 1532819 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].[O-:12][Mn](=O)(=O)=O.[K+].[OH2:18]>N1C=CC=CC=1>[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:12])=[O:18]

Participants

5

Reactant 3

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

Product 1

HCID 3135342-Bromo-4-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-4-nitrotoluene (5.0 g, 23.14 mmol) was dissolved in 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. The crude product was dissolved in aqueous NaOH and washed with hexanes. The aqueous phase was made acidic and the product was extracted into ethyl acetate. The ethyl acetate solutions were combined and dried over Na2SO4 and the solvent was removed in vacuo to provide the desired product (3.72 g): m.p. 158-160° C.; 1H NMR (CD3OD) d 7.81 (1H, d, J=8.5 Hz), 8.08 (1H, d, J=8.5 Hz), 8.30 (1H, s); 13C NMR (CD3OD) d 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. temperatureThe mixture was then heated
  2. temperatureunder reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. washwashed with boiling water
  5. extractionmade acidic and extracted into ethyl acetate
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed in vacuo
  8. dissolutionThe crude product was dissolved in aqueous NaOH
  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

Sources & evidence

ORD record
ord-23c2a9f207c84d16b50c1d036800b068
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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