Ammonium Chloride → 4-(2-Fluorophenoxy)aniline

HRID 1854953Notes

Reaction equation

HRID 1854953 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1.[NH4+].[Cl-]>CO.O.[Fe]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 579749991-Fluoro-2-(4-nitrophenoxy)benzene

Product 1

HCID 51260734-(2-Fluorophenoxy)anilineYield 73.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

Into a 250 ml, 3-necked round-bottom flask, was placed a solution of 1-fluoro-2-(4-nitrophenoxy)benzene (5 g, 21.44 mmol, 1.00 equiv) in methanol/H2O (2/1=V/V) (100 mL), and NH4Cl (1 g, 18.70 mmol, 0.87 equiv). This was followed by the addition of Fe (7 g, 5.83 equiv), in portions at 80° C. in 20 min. The resulting solution was stirred for 1 h at reflux in an oil bath. The reaction mixture was cooled in a water bath. The solids were filtered out and the filtrate was concentrated under vacuum. The resulting solution was extracted with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum to give 3.2 g (73%) of 4-(2-fluorophenoxy)aniline as a light yellow solid.

Workup

  1. temperatureat reflux in an oil bath
  2. temperatureThe reaction mixture was cooled in a water bath
  3. filtrationThe solids were filtered out
  4. concentrationthe filtrate was concentrated under vacuum
  5. extractionThe resulting solution was extracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-073b6f0f40ad4f68a38fe7179f3c6e10
Source dataset
uspto-grants-2015_02
Patent number
US08962831B2

Reaction notes

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