Ammonium Chloride → 4-(Benzyloxy)-2-fluoroaniline

HRID 388020

反応式

HRID 388020 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([F:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([F:18])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzene

生成物 1

HCID 114998094-(Benzyloxy)-2-fluoroaniline収率 81.35%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

After dissolving the 4-benzyloxy-2-fluoronitrobenzene crude crystals (16.06 g, 63.65 mmol) in ethanol (1000 ml) and water (200 ml), electrolytic iron powder (14.0 g, 254.60 mmol) and ammonium chloride (27.2 g, 509.20 mmol) were added and the mixture was heated to reflux for 4.5 hours. The reaction solution was cooled to near room temperature, the insoluble portion was filtered off, washing was performed with ethanol and the solvent of the filtrate was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was adsorbed onto silica gel and purified by silica gel column chromatography (hexane-ethyl acetate system) to obtain the title compound (11.25 g, 51.78 mmol, 81.35%) as a brown oil.

後処理

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 4.5 hours
  4. filtrationthe insoluble portion was filtered off
  5. washwashing
  6. distillationthe solvent of the filtrate was distilled off under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with saturated saline
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. custompurified by silica gel column chromatography (hexane-ethyl acetate system)

出典と根拠

ORDレコード
ord-4d1e4b4af20942f88e0b8630084c9314
出典データセット
uspto-grants-2013_02
特許番号
US08372981B2

関連ノート

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