Methyl iodide → Methyl 4-fluoro-3-nitrobenzoate

HRID 555288Notes

Reaction equation

HRID 555288 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:14][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 5219721Methyl 4-fluoro-3-nitrobenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-3-nitrobenzoic acid (16.0 g, 0.0864 mol) in dry DMF (100 mL) was added with stirring potassium carbonate (59.0 g, 0.43 mol) followed by methyl iodide (24.5 g, 0.173 mol) and the mixture was stirred for 3 h at ambient temperature. The reaction mixture was diluted with ice water (500 mL), extracted with EtOAc (3×100 mL) and the combined organic phases were washed with water (3×100 mL) and saturated brine solution (100 mL). The organic phase was dried (Na2SO4) and the solvent evaporated affording 17.0 g (99%) of 4-fluoro-3-nitro-benzoic acid methyl ester.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washthe combined organic phases were washed with water (3×100 mL) and saturated brine solution (100 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-0e473d5df360485895a5b4cc0d1e724c
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

Loading…