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 2188942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2188942
[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-9f34236b27ae4e04b1baa2fb85b5f149
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324207B2

Notizen zur Reaktion

Wird geladen…