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

HRID 230708

Reaction equation

HRID 230708 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].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]

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
60 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-0a65bf957c504fd4a9138c474b2d88c4
Source dataset
uspto-grants-2009_07
Patent number
US07566773B2

Linked notes

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