Acetone → 2-Amino-4-Bromophenol

HRID 236809

Reaktionsgleichung

Reaktionsgleichung von HRID 236809
BrC1C=CC(O)=CC=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([N+:17]([O-])=O)[CH:11]=1.CC(C)=O.[O-]S(S([O-])=O)=O.[Na+].[Na+]>O>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH:11]=1)[NH2:17]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 78084-BromophenolHCID 243644-Bromo-2-nitrophenol2×HCID 24489Sodium Dithionite

Produkt 1

HCID 3518402-Amino-4-Bromophenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A portion of 4-bromophenol is converted to 4-bromo-2-nitrophenol by the method described in Rec. Trav. Chim. 29, 187(1910). A 28 g. portion of 4-bromo-2-nitrophenol is dissolved in 280 ml. of acetone. A 280 ml. portion of water and 112 g. of Na2S2O4 are added with stirring. The mixture is refluxed for 2 hours, cooled to room temperature and extracted six times with ether. The ether extracts are washed twice with brine, dried over magnesium sulfate and recrystallized from a mixture of charcoal and 400 ml. of water giving an oil. This oil is redissolved in 600 ml. of water, cooled to 0° C. and filtered giving 5-bromo-2-hydroxyaniline as tan crystals.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 2 hours
  2. extractionextracted six times with ether
  3. washThe ether extracts are washed twice with brine
  4. dry with materialdried over magnesium sulfate
  5. customrecrystallized from a mixture of charcoal and 400 ml
  6. dissolutionThis oil is redissolved in 600 ml
  7. temperatureof water, cooled to 0° C.
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-8ead2872a36346ddb7420170ff90aa9e
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04157444

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