Water → Methyl 2-chloro-3-nitrobenzoate

HRID 1612048Notes

Reaction equation

HRID 1612048 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].IC.[C:16](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 198702-Chloro-3-nitrobenzoic acid

Product 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoateYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-3-nitrobenzoic acid (20.16 g, 100 mmol), iodomethane (15.6 g, 110 mmol), and potassium carbonate (15.0 g, 108.5 mmol) in DMF (100 mL) was stirred at room temperature for 48 h. The mixture was poured into 1.5 liters of H2O. The resultant precipitate was collected by filtration, washed with H2O, and dried in vacuo to afford 20.0 g (93%) of the title compound 2-chloro-3-nitrobenzoic acid, methyl ester as a white solid (MW 215.59).

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with H2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-6e1dee451a7e416088a0b3d4aa6347f1
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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