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 2188942ノート

反応式

HRID 2188942 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f34236b27ae4e04b1baa2fb85b5f149
出典データセット
uspto-grants-2012_12
特許番号
US08324207B2

反応ノート

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