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 2420917Notes

Reaction equation

HRID 2420917 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 133206092-(3-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-olYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fb2f6937deb64027995a2b1dd879aea3
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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