Chloric acid → 4-tert-Butyl-3-chloroaniline

HRID 1350838

反応式

HRID 1350838 の反応式
Cl(O)(=O)=O.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[Cl:18])([CH3:8])([CH3:7])[CH3:6]>[Zn].C(O)(=O)C>[C:5]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[Cl:18])([CH3:8])([CH3:6])[CH3:7]

参加物

5

反応物 2

HCID 19654Chloric acidHCID 210974512-Chloro-1-(1,1-dimethylethyl)-4-nitrobenzene

生成物 1

HCID 119590404-tert-Butyl-3-chloroaniline収率 48.9%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

反応条件

温度
60 °C

実験手順

To an acetic acid (7 ml) and conc. chloric acid (2 ml) solution of 1-tert-butyl-2-chloro-4-nitrobenzene (1.67 g, 7.8 mmol) was added zinc powder (4.1 g, 62 mmol) at 60° C. The reaction mixture was stirred at 60° C. for 1 hour. Zinc powder was filtered off and washed with H2O. The filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate and then the organic layer washed with saturated aqueous solution of sodium bicarbonate and brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane=¼ to furnish 0.7 g (48% yield) of the title compound as a brown oil.

後処理

  1. filtrationZinc powder was filtered off
  2. washwashed with H2O
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic layer washed with saturated aqueous solution of sodium bicarbonate and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. customto separate solvent and sodium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customto give a residue, which
  11. washeluted with ethyl acetate/hexane=¼

出典と根拠

ORDレコード
ord-bcade05963d541e08082c37d597bd64d
出典データセット
uspto-grants-2007_05
特許番号
US07214824B2

関連ノート

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