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

HRID 2094478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2094478
[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-a1e1f0ee3caf40f7b52cdf8ac4188011
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445522B2

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