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

HRID 1350838

Reaktionsgleichung

Reaktionsgleichung von HRID 1350838
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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 119590404-tert-Butyl-3-chloroanilineAusbeute 48,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bcade05963d541e08082c37d597bd64d
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214824B2

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