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

HRID 1869320Notes

Reaction equation

HRID 1869320 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-db5f3e092cbb41f4bf7d1311f0b0bb6e
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

Loading…