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Acetic Acid → 2-Amino-4-((trifluoromethyl)thio)phenol

HRID 1913716
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1913716
[N+:1]([C:4]1[CH:9]=[C:8]([S:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[OH:15])([O-])=O.C(OCC)(=O)C.C(O)(=O)C>[Fe].O>[NH2:1][C:4]1[CH:9]=[C:8]([S:10][C:11]([F:14])([F:12])[F:13])[CH:7]=[CH:6][C:5]=1[OH:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 265966692-Nitro-4-((trifluoromethyl)thio)phenol

Produkt 1

HCID 230231052-Amino-4-((trifluoromethyl)thio)phenolAusbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962
Water
Lösungsmittel
2×

Versuchsvorschrift

A mixture of 5.49 g of 2-nitro-4-(trifluoromethylthio)phenol and 10 ml of ethyl acetate was added dropwise to a mixture, which was heated to 80° C., of 6.4 g of electrolytic iron, 10 ml of acetic acid and 20 ml of water. The reaction mixture was stirred for 30 minutes. The mixture was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate twice. 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 2.0 g of 2-amino-4-(trifluoromethylthio)phenol.

Aufarbeitung

  1. additionwas added dropwise to a mixture, which
  2. extractionfollowed by extraction with ethyl acetate twice
  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-e1349a8ccdec4c42aeb17ac13badd779
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08609705B2

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