Methyl iodide → Methyl 5-fluoro-2-methyl-3-nitrobenzoate

HRID 1443137Notes

Reaction equation

HRID 1443137 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([F:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CI.[C:17](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:17][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([F:14])[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 179850235-Fluoro-2-methyl-3-nitrobenzoic acid

Product 1

HCID 44203026Methyl 5-fluoro-2-methyl-3-nitrobenzoateYield 25.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.56 g (42.99 mmol) of 2-methyl-5-fluoro-3-nitrobenzoic acid is added in 76 ml of N,N-dimethylformamide and mixed with 9.15 g (64.48 mmol) of methyl iodide and 8.91 g (64.48 mmol) of potassium carbonate. After 65 hours of stirring at room temperature, the reaction mixture is added to ice water and extracted several times with ethyl acetate. The combined organic extracts are washed with water and brine. After drying (sodium sulfate), desiccant is suctioned out, and the solvent is spun off. Repeated chromatography on silica gel (mobile solvent:ethyl acetate/hexane) yields the desired compound, specifically in a yield of 25.9% (2.37 g).

Workup

  1. extractionextracted several times with ethyl acetate
  2. washThe combined organic extracts are washed with water and brine
  3. dry with materialAfter drying (sodium sulfate)

Sources & evidence

ORD record
ord-cd9d89baa8a6415fa2502797742bac6b
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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