Acetic Acid → 3-Chloro-4-(3-chlorophenoxy)aniline

HRID 38242

Reaktionsgleichung

Reaktionsgleichung von HRID 38242
C(O)(=O)C.[Cl:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1>O.CCO.[Fe]>[Cl:5][C:6]1[CH:11]=[C:10]([CH:9]=[CH:8][C:7]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[NH2:12]

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 2752072-Chloro-1-(3-chlorophenoxy)-4-nitrobenzene

Produkt 1

HCID 176055343-Chloro-4-(3-chlorophenoxy)anilineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

According to Scheme 3 Step 2: A suspension of iron (5.07 mmol, 283 mg), acetic acid (1.22 mmol, 70 μL) and of 2-chloro-1-(3-chlorophenoxy)-4-nitrobenzene (1.02 mmol, 288 mg) in water/EtOH (1:1, 8 mL) was stirred at 80° C. for 30 minutes. After evaporation of EtOH, the aqueous phase was basified with a saturated solution of NaHCO3 and was extracted with AcOEt. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure to yield 3-chloro-4-(3-chlorophenoxy)aniline (1.02 mmol, 258 mg, 100%) as a solid. The product was used without further purification.

Aufarbeitung

  1. customAfter evaporation of EtOH
  2. extractionwas extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-077c9c4ea8274fb796a20617fa6ba2d7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524726B2

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