1,1,1,3,3,3-Hexafluoro-2-(3-nitrophenyl)propan-2-ol → 2-(3-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 1442816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1442816
[F:1][C:2]([F:19])([F:18])[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:15][C:11]1[CH:10]=[C:9]([C:3]([OH:8])([C:2]([F:1])([F:18])[F:19])[C:4]([F:5])([F:6])[F:7])[CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 2

HCID 2795821,1,1,3,3,3-Hexafluoro-2-(3-nitrophenyl)propan-2-olHCID 2723923Ammonium formate

Produkt 1

HCID 133206092-(3-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-olAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1,1,1,3,3,3-hexafluoro-2-(3-nitrophenyl)propan-2-ol (6.0 g, 21 mmol) in ethanol (60 mL) was added ammonium formate (6.0 g) and Pd/C (10%, 600 mg). The mixture was heated at reflux for 5 min and was cooled to room temperature. The Pd catalyst was removed via filtration through Celite using ethanol. The combined filtrate was evaporated to dryness and the residue was washed with CH2Cl2 to yield 2-(3-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (4.1 g, 67% over two steps). 1H NMR (400 MHz, DMSO-d6) δ 8.37 (s, 1H), 7.11 (t, J=7.9 Hz, 1H), 6.93 (s, 1H), 6.77 (d, J=7.8 Hz, 1H), 6.65 (dd, J=8.0, 1.6 Hz, 1H), 5.34 (s, 2H). MS (ESI) m/e (M+H+) 260.1.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 min
  3. customThe Pd catalyst was removed via filtration through Celite
  4. customThe combined filtrate was evaporated to dryness
  5. washthe residue was washed with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-69053124efc442c6a63df9e0f368191d
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659268B2

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