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

HRID 1662941

Reaction equation

HRID 1662941 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

HCID 122241571-(5-Bromo-2-nitrophenyl)ethanone

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2584ff91657842e0ab26364f0533adf3
Source dataset
uspto-grants-2011_10
Patent number
US08034747B2

Linked notes

Loading…