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

HRID 1023507노트

반응식

HRID 1023507 반응식
[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

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 672358223-Chloro-5-fluorophenyl 4-nitrophenyl ether2회

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-751a9cc5caac4c44a2d89e4bf72fde29
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722695B2

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