Water → 1-Fluoro-2,3-dimethoxybenzene

HRID 1295939Notes

Reaction equation

HRID 1295939 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[C:3]=1O.[CH3:10]I.[C:12](=[O:15])([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([O:5][CH3:10])[C:3]=1[O:15][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 677643-Fluorocatechol

Product 1

HCID 27589791-Fluoro-2,3-dimethoxybenzeneYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving the 3-fluorocatechol (30 g, 0.234 mol) in dimethylformamide (400 ml), methyl iodide (32 ml, 0.515 mol) and potassium carbonate (80.7 g, 0.515 mol) were added while stirring on ice, and the stirring was continued at room temperature for 18 hours. Water (500 ml) was added and extraction was performed with diethyl ether (400 ml×2), and then after washing the combined organic layers with brine (400 ml) and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to yield the title compound as a light yellow liquid (34 g, 93%).

Workup

  1. additionwere added
  2. extractionextraction
  3. washafter washing the combined organic layers with brine (400 ml)
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-298593f07ce946959b490098ab705950
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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