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

HRID 853545

反応式

HRID 853545 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 brine 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 brine
  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-dfa930a0306449e6bb5e6db3a61d4081
出典データセット
uspto-grants-2007_08
特許番号
US07253286B2

関連ノート

読み込み中…