Water → Methyl 2,5-dichloro-3-nitrobenzoate

HRID 2208702Notes

Reaction equation

HRID 2208702 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Cl:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15](=O)([O-])[O-].[Na+].[Na+].CI.O>CN(C=O)C>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Cl:14])=[CH:7][C:3]=1[C:4]([O:6][CH3:15])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 69512,5-Dichloro-3-nitrobenzoic acidHCID 10340Sodium Carbonate

Product 1

HCID 36821Methyl 2,5-dichloro-3-nitrobenzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To stirred solution of 2,5-dichloro-3-nitrobenzoic acid (3.2 g, 13.67 mmol) in DMF (30 mL) was added sodium carbonate (4.3 g, 40.56 mmol) and methyl iodide (9.7 g, 68.30 mmol). The reaction mixture was heated at 60° C. for 18 h. On completion, water was added to the reaction mixture, and the product was extracted using DCM. The combined organic layers were dried and concentrated under reduced pressure to give methyl 2,5-dichloro-3-nitrobenzoate (3 g, 90%).

Workup

  1. extractionthe product was extracted
  2. customThe combined organic layers were dried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-834851548c254b8cbf6df7ba8a65a6f4
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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