Nitric Acid → 2-(2,6-Dichloro-3-nitrophenyl)acetonitrile

HRID 270691Notes

Reaction equation

HRID 270691 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]#[N:11].[N+:12]([O-])([OH:14])=[O:13]>ClCCl.OS(O)(=O)=O>[Cl:1][C:2]1[C:7]([N+:12]([O-:14])=[O:13])=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]#[N:11]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 76678(2,6-Dichlorophenyl)acetonitrile

Product 1

HCID 598338582-(2,6-Dichloro-3-nitrophenyl)acetonitrileYield 82.4%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,6-dichloro-phenyl-acetonitrile (15.0 g, 80.62 mmol) in the dichloromethane (50 mL) and H2SO4 (40 mL) is added (slowly) a mixture of H2SO4 (14 mL) and HNO3 (5.5 mL) at 0° C. The reaction mixture is stirred at 0° C. for 20 minutes, warned to room temperature for half hour, and then concentrated to remove organic solvent. The solution is poured into a beaker containing ice-water (400 mL) to give a crystalline precipitate, which is collected by vacuum filtration and washed with water to afford the product (20.44 g, 82.4%).

Workup

  1. waitwarned to room temperature for half hour
  2. concentrationconcentrated
  3. customto remove organic solvent
  4. additionThe solution is poured into a beaker
  5. additioncontaining ice-water (400 mL)
  6. customto give a crystalline precipitate, which
  7. filtrationis collected by vacuum filtration
  8. washwashed with water

Sources & evidence

ORD record
ord-5cef8f316395478d8ffe4cffcc609f28
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Reaction notes

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