Water → 2-Bromo-4-nitrobenzoic acid

HRID 325205

반응식

HRID 325205 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 3135342-Bromo-4-nitrobenzoic acid

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-10da3d6c15854c66bb5146022d9045cf
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06221865B1

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