Ethanone, 1-(5-amino-2-nitrophenyl)- → 1-(5-Bromo-2-nitrophenyl)ethanone

HRID 230708

Reaktionsgleichung

Reaktionsgleichung von HRID 230708
[C:1]([C:4]1[CH:5]=[C:6](N)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])(=[O:3])[CH3:2].N([O-])=O.[Na+].[BrH:18].O>>[C:1]([C:4]1[CH:5]=[C:6]([Br:18])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])(=[O:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 6420386Ethanone, 1-(5-amino-2-nitrophenyl)-HCID 22326455Hydrobromide monohydrateHCID 23668193Sodium Nitrite

Produkt 1

HCID 122241571-(5-Bromo-2-nitrophenyl)ethanoneAusbeute 75 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

10 mmol of 3-acetyl-4-nitro-aminobenzene as a starting material was added to 100 mL of HBr/H2O (1/2, v/v) and a sodium nitrite solution was slowly added dropwise thereto in an ice bath. The reaction mixture was stirred at 60° C. for 2 hours. When the reaction was completed, the precipitate was filtered off. The filtrate was neutralized with 1N NaOH, extracted with EtOAc, dried over anhydrous sodium sulfate, distilled under reduced pressure and purified by silica gel column chromatography (hexane/EtOAc=2/1) to obtain the desired 3-acetyl-4-nitro-bromobenzene as a yellow oil (75%).

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. extractionextracted with EtOAc
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. custompurified by silica gel column chromatography (hexane/EtOAc=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-0a65bf957c504fd4a9138c474b2d88c4
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566773B2

Verknüpfte Notizen

Wird geladen…