Water → 2-Bromo-4-nitrobenzoic acid

HRID 325205

反応式

HRID 325205 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 3135342-Bromo-4-nitrobenzoic acid

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-10da3d6c15854c66bb5146022d9045cf
出典データセット
uspto-grants-2001_04
特許番号
US06221865B1

関連ノート

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