Ethanol → 2-(Benzyloxy)-4-fluoroaniline

HRID 576062ノート

反応式

HRID 576062 の反応式
C(O)C.[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N+:19]([O-])=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[NH4+]>[Fe].O>[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[NH2:19])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

参加物

6

反応物 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

生成物 1

HCID 167713362-(Benzyloxy)-4-fluoroaniline

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To an ethanol (25 mL)-water (25 mL) mixture containing 2-(benzyloxy)-4-fluoro-1-nitrobenzene obtained were added iron (2.79 g, 50.0 mmol) and ammonium chloride (535 mg, 10.0 mmol) at room temperature, and the mixture was stirred at 100° C. for 1 hr. After cooling to room temperature, the reaction mixture was filtered through Celite (registered trademark) and the filtrate was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the resulting residue, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to afford the title compound as a brownish red oil (1.26 g).

後処理

  1. customobtained
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtered through Celite (registered trademark)
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionSaturated aqueous sodium hydrogen carbonate solution was added to the resulting residue
  6. extractionthe mixture was extracted three times with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationthe desiccant was filtered off
  10. concentrationfollowed by concentration under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

出典と根拠

ORDレコード
ord-d925c7f160fe43ee83497d4eb1e808fe
出典データセット
uspto-grants-2015_05
特許番号
US09035059B2

反応ノート

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