Reaktion #45981

Reaktionsgleichung

nitro

4-(2,4-dichloro-phenoxy)-1-nitrobenzene

SnCl2.2H2O

→

4-(2,4-dichloro-phenoxy)aniline

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturunder reflux until completion
3. 3
   SonstigeThe solvent was removed in vacuuo
4. 4
   workup.ADDITIONthe residue was treated with 4.0 N aqueous NaOH to pH˜8
5. 5
   ExtraktionThe residue was extracted with EtOAc (2×50 mL)
6. 6
   Waschenwashed with 1.0 N aqueous NaOH (50 mL), brine (50 mL)
7. 7
   Trocknendried over sodium sulfate
8. 8
   SonstigeThe solvent was removed in vacuuo

Vorschrift

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.

Quelle