Acetic Acid → 2-Amino-4-chloro-3-trifluoromethylphenol

HRID 884960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 884960
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[C:3]=1[C:12]([F:15])([F:14])[F:13].C(OCC)(=O)C.C(O)(=O)C>[Fe].O>[NH2:9][C:4]1[C:3]([C:12]([F:13])([F:14])[F:15])=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[OH:8]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 581482394-Chloro-2-nitro-3-(trifluoromethyl)phenol

Produkt 1

HCID 581482802-Amino-4-chloro-3-trifluoromethylphenolAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 1.57 g of 4-chloro-2-nitro-3-trifluoromethylphenol and 5 ml of ethyl acetate was added dropwise to a mixture, which was heated to 80° C., of 1.8 g of electrolytic iron, 7 ml of acetic acid and 7 ml of water, which was stirred for 30 minutes. The mixture was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate. The combined organic layers were washed with water, a saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.1 g of 2-amino-4-chloro-3-trifluoromethylphenol.

Aufarbeitung

  1. additionwas added dropwise to a mixture, which
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b9a4be00583a443b981c1d02fae5fbcd
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242133B2

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