1,4-Dibromo-2-nitrobenzene → 4-Bromo-2-nitrobenzonitrile

HRID 1791215Notes

Reaction equation

HRID 1791215 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([Cu])#[N:13]>CC(N(C)C)=O.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]#[N:13])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 2

HCID 770041,4-Dibromo-2-nitrobenzeneHCID 178418546HCID 178418546, compound

Product 1

HCID 2925354-Bromo-2-nitrobenzonitrile

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

Stir the mixture of 1,4-dibromo-2-nitro-benzene (3.56 mmol)and CuCN (3.74 mmol) in DMA (4 ml) at 100° C. for 5hours. Cool to room temperature, dilute with EtOAc, filter through celite, wash the organic layer with brine, dry over Na2SO4, and concentrate under vacuum. Purify the residue by flash chromatography (4:1 hexanes/EtOAc) to give 4-bromo-2-nitro-benzonitrile.

Workup

  1. filtrationfilter through celite
  2. washwash the organic layer with brine
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate under vacuum
  5. customPurify the residue by flash chromatography (4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-4080763d33fc4969b23659b3cd2ed48e
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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