Dichloromethane → Methyl 2,6-dichloro-4-nitrobenzoate

HRID 1060484Notes

Reaction equation

HRID 1060484 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([Cl:14])[C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH2:19](Cl)Cl>>[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([Cl:14])[C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 225719382,6-Dichloro-4-nitrobenzoic acid

Product 1

HCID 22571909Methyl 2,6-dichloro-4-nitrobenzoateYield 80%

Procedure

To 2,6-dichloro-4-nitrobenzoic acid (12.8 g, U.S. Pat. No. 3,423,475) was added anhydrous CH2Cl2 (60 mL) and thionyl chloride (40 mL) then the resulting mixture was refluxed for 19 h. The mixture was allowed to cool to room temperature and evaporated. Additional CH2Cl2 (10 mL) was added and the solution was evaporated. MeOH (100 mL) was added to the residue and the mixture was refluxed for 17 h. The mixture was allowed to cool to room temperature and placed in an ice-bath. The precipitated solid was collected by filtration to give methyl 2,6-dichloro-4-nitrobenzoate (10.8 g, 80%).

Workup

  1. temperaturethe resulting mixture was refluxed for 19 h
  2. customevaporated
  3. additionAdditional CH2Cl2 (10 mL) was added
  4. customthe solution was evaporated
  5. additionMeOH (100 mL) was added to the residue
  6. temperaturethe mixture was refluxed for 17 h
  7. temperatureto cool to room temperature
  8. customplaced in an ice-bath
  9. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-50b3fa2aa25947b9b1a6e77e8ef78100
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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