1,4-Dibromo-2-nitrobenzene → 4,4'-Dibromo-2,2'-dinitro-1,1'-biphenyl

HRID 71905

Reaction equation

HRID 71905 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]>CN(C=O)C.[Cu]>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 1

HCID 770041,4-Dibromo-2-nitrobenzene

Product 1

HCID 100466484,4'-Dibromo-2,2'-dinitro-1,1'-biphenylYield 76%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

The mixture of 1,4-dibromo-2-nitro-benzene (25 g, 89 mmol) and copper powder (12.5 g, 197 mmol) in DMF (150 ml) was heated at 137 C for 2 hours. The mixture was cooled to 25° C. and was quenched with water. The mixture was extracted with EtOAc (2×). The combined organic solution was washed with water and brine and was dried with Na2SO4. Concentration and purification by flash column chromatography (hexanes/EtOAc) gave 4,4′-dibromo-2,2′-dinitro-biphenyl (13.6 g).

Workup

  1. temperaturewas heated at 137 C for 2 hours
  2. customwas quenched with water
  3. extractionThe mixture was extracted with EtOAc (2×)
  4. washThe combined organic solution was washed with water and brine
  5. dry with materialwas dried with Na2SO4
  6. concentrationConcentration and purification by flash column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-d63499b6a64f48e1953ce7656e13f849
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Linked notes

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