Ammonium Chloride → 4-[(3-Chloro-5-fluorophenyl)oxy]aniline

HRID 1505303ノート

反応式

HRID 1505303 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([Cl:18])[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>C1COCC1.O.[Fe]>[Cl:18][C:13]1[CH:12]=[C:11]([O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:16]=[C:15]([F:17])[CH:14]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 672358223-Chloro-5-fluorophenyl 4-nitrophenyl ether2 回

生成物 1

HCID 672366794-[(3-Chloro-5-fluorophenyl)oxy]aniline収率 95.6%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-chloro-5-fluorophenyl 4-nitrophenyl ether (Intermediate 5, 2.38 g) in THF (40 mL) and water (10 mL) was added Fe power (11.2 g, 200 mmol) and ammonium chloride (10.7 g, 200 mmol). The reaction mixture was heated at reflux for 4 hours. After filtration, the solvent was concentrated to give a residue and poured into 50 mL of water. The mixture was extracted with ethyl acetate (3 times 50 mL) and the combined organic phases were washed and dried over magnesium sulphate. Removal of the solvent afforded the title compound (2.02 g) which was directly used in the next step.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. filtrationAfter filtration
  4. concentrationthe solvent was concentrated
  5. customto give a residue
  6. extractionThe mixture was extracted with ethyl acetate (3 times 50 mL)
  7. washthe combined organic phases were washed
  8. dry with materialdried over magnesium sulphate
  9. customRemoval of the solvent

出典と根拠

ORDレコード
ord-3d754ae8c13e47ad929180a68c1a6b3e
出典データセット
uspto-grants-2015_12
特許番号
US09216967B2

反応ノート

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