Methyl iodide → Methyl 6-fluoro-2-methyl-3-nitrobenzoate

HRID 706579Notes

Reaction equation

HRID 706579 reaction equation
[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:11])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[F:1][C:2]1[C:7]([C:8]([O:10][CH3:15])=[O:9])=[C:6]([CH3:11])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 593345776-Fluoro-2-methyl-3-nitrobenzoic acid

Product 1

HCID 59334469Methyl 6-fluoro-2-methyl-3-nitrobenzoateYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-fluoro-2-methyl-3-nitrobenzoic acid (21.2 g, 0.107 mol), powdered potassium carbonate (36.8, 0.266 mol) in DMF (200 mL) was added methyl iodide (37.8 g, 0.266 mol). The mixture was stirred at ambient temperature for 16 hours, then diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (20% ethyl acetate/hexane) afforded 12.6 g (56%) of the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1a2bbd2066946aeac5e1cc453d6dc33
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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