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

HRID 1662941

Reaktionsgleichung

Reaktionsgleichung von HRID 1662941
[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].[BrH:14].O.N([O-])=O.[Na+]>>[C:1]([C:4]1[CH:5]=[C:6]([Br:14])[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)ethanone

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In the ice bath, the starting material, about 10 mmol of 3-acetyl-4-nitro-aminobenzene was added into HBr/H2O (about 100 mL, 1/2, v/v), and sodium nitrite solution was gradually added. The solution was stirred at about 60° C. for about 2 hours. After the reaction was completed, the precipitate was filtered. The filtered solution was neutralized with about 1N NaOH, and extracted with EtOAc. Then the extracted material was dried with sodium sulfate anhydride. Next, the dried material was distilled under reduced pressure. Then, 3-acetyl-4-nitro-bromobenzene was obtained in a form of about 75% yellow oil using silica gel column chromatography (Hexane/EtOAc=2/1).

Aufarbeitung

  1. filtrationthe precipitate was filtered
  2. extractionextracted with EtOAc
  3. dry with materialThen the extracted material was dried with sodium sulfate anhydride
  4. distillationNext, the dried material was distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2584ff91657842e0ab26364f0533adf3
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08034747B2

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