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

HRID 1505303Notes

Reaction equation

HRID 1505303 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3d754ae8c13e47ad929180a68c1a6b3e
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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