Reaktion #412387

Reaktionsgleichung

2-Bromo-4-nitrotoluene

KMnO4

water

→

desired product

2-Bromo-4-nitrobenzoic acid

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then heated
2. 2
   Temperaturunder reflux overnight
3. 3
   FiltrationThe reaction mixture was filtered
4. 4
   Waschenwashed with boiling water
5. 5
   Extraktionmade acidic and extracted into ethyl acetate
6. 6
   Trocknendried over Na2SO4
7. 7
   Sonstigethe solvent was removed in vacuo
8. 8
   workup.DISSOLUTIONThe crude product was dissolved in aqueous NaOH
9. 9
   Waschenwashed with hexanes
10. 10
    Extraktionthe product was extracted into ethyl acetate
11. 11
    Trocknendried over Na2SO4
12. 12
    Sonstigethe solvent was removed in vacuo

Vorschrift

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.

Quelle