Acetic Acid → 2-Amino-4-chloro-5-(trifluoromethyl)phenol

HRID 1913720

Reaktionsgleichung

Reaktionsgleichung von HRID 1913720
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([OH:12])=[C:4]([N+:13]([O-])=O)[CH:3]=1.C(OCC)(=O)C.C(O)(=O)C>[Fe].O>[NH2:13][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][C:5]=1[OH:12]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 668796884-Chloro-2-nitro-5-(trifluoromethyl)phenol

Produkt 1

HCID 668804782-Amino-4-chloro-5-(trifluoromethyl)phenolAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 2.3 g of 4-chloro-2-nitro 5-trifluoromethylphenol and 10 ml of ethyl acetate was added dropwise to a mixture, which was heated to 80° C., of 2.6 g of electrolytic iron, 10 ml of acetic acid and 20 ml of water, and then the reaction mixture was stirred for one hour. 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 1.7 g of 2-amino-4-chloro-5-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-ce85c188db534853a7ebc1de2f3aea15
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609705B2

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