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

HRID 1639774Notes

Reaction equation

HRID 1639774 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+].IC.O>CN(C)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 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 593345776-Fluoro-2-methyl-3-nitrobenzoic acid

Product 1

HCID 59334469Methyl 6-fluoro-2-methyl-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A crudely purified product (20.7 g) of 6-fluoro-2-methyl-3-nitrobenzoic acid was dissolved in N,N-dimethylformamide (208 mL), and potassium carbonate (28.7 g, 208 mmol) and iodomethane (8.45 mL, 135 mmol) were added at room temperature. The reaction solution was stirred at room temperature for 12 hr, and poured into water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound as a crudely purified product (21.0 g, yield 95%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5f1bac50446a4a15bf85ee53617fdfc6
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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