Ammonium Chloride → 4-(2-Fluorophenoxy)aniline

HRID 1843380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1843380
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 51260734-(2-Fluorophenoxy)anilineAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customInto a 250 mL 3-necked round-bottom flask, was placed
  2. temperatureat reflux in an oil bath
  3. temperatureThe reaction mixture was cooled in a water bath
  4. filtrationThe solids were filtered out
  5. concentrationthe filtrate was concentrated under vacuum
  6. extractionThe resulting solution was extracted with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-389d5d0cdf8941109fe7b3b340e7c977
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946241B2

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