Nitrofen → 4-(2,4-Dichlorophenoxy)benzenamine

HRID 17703

Reaktionsgleichung

Reaktionsgleichung von HRID 17703
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1.O.O.Cl[Sn]Cl>CO>[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 15787NitrofenHCID 61436Stannous chloride dihydrate

Produkt 1

HCID 269404-(2,4-Dichlorophenoxy)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The nitro intermediate (10 mmol) obtained above was dissolved in MeOH (20 mL), and treated with SnCl2.2H2O (50 mmol), according to General Procedure I. The reaction mixture was heated under reflux until completion, as indicated by TLC or HPLC. The solvent was removed in vacuuo and the residue was treated with 4.0 N aqueous NaOH to pH˜8. The residue was extracted with EtOAc (2×50 mL), washed with 1.0 N aqueous NaOH (50 mL), brine (50 mL) and dried over sodium sulfate. The solvent was removed in vacuuo to afford the desired 4-(2,4-dichloro-phenoxy)aniline, which was used directly for further transformation without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux until completion
  3. customThe solvent was removed in vacuuo
  4. additionthe residue was treated with 4.0 N aqueous NaOH to pH˜8
  5. extractionThe residue was extracted with EtOAc (2×50 mL)
  6. washwashed with 1.0 N aqueous NaOH (50 mL), brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed in vacuuo

Quellen und Nachweise

ORD-Eintrag
ord-dff2ecc4c66849b99cef2be126d5da78
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737285B2

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