1,3-Dibromo-2-methyl-4-nitrobenzene → 3-Bromo-2-methyl-6-nitrobenzonitrile

HRID 653537Notes

Reaction equation

HRID 653537 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Br:11])[C:3]=1[CH3:12].[Cu][C:14]#[N:15]>CN1CCCC1=O.ClCCl>[Br:11][C:4]1[C:3]([CH3:12])=[C:2]([C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1)[C:14]#[N:15]

Participants

5

Reactant 2

HCID 138854011,3-Dibromo-2-methyl-4-nitrobenzeneHCID 178418546HCID 178418546, compound

Product 1

HCID 138854073-Bromo-2-methyl-6-nitrobenzonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2,6-dibromo-3-nitrotoluene (1.0 g, 3.4 mmol) in 14 ml of N-methylpyrrolidinone was added 0.323 g of freshly prepared copper (I) cyanide. The reaction was stirred and heated at a temperature of 150° C. under a nitrogen atmosphere for a period of three hours. After this period, the reaction mixture was cooled to room temperature, diluted with dichloromethane, and washed with 10% aqueous sodium thiosulfate solution. The organic layer was separated, dried, and concentrated under vacuum to remove the solvent. The residue was chromatographed on silica gel, eluting with 20% ethyl acetate/80% hexane, to afford 0.293 g of 3-bromo-2-methyl-6-nitrobenzonitrile as a yellow-white crystalline solid, mp 116°-118° C.

Workup

  1. waitAfter this period
  2. temperaturethe reaction mixture was cooled to room temperature
  3. washwashed with 10% aqueous sodium thiosulfate solution
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customto remove the solvent
  8. customThe residue was chromatographed on silica gel
  9. washeluting with 20% ethyl acetate/80% hexane

Sources & evidence

ORD record
ord-aaef7cdc90a04753b4ef5fcb44622045
Source dataset
uspto-grants-1987_06
Patent number
US04677219

Reaction notes

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