Diethyl Ether → methyl 2-fluoro-6-methoxybenzoate

HRID 1870297Notes

Reaction equation

HRID 1870297 reaction equation
[F:1][C:2]1[CH:3]=CC=[C:6](O)[C:7]=1C(O)=O.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].[CH3:18]I.C[CH2:21][O:22][CH2:23][CH3:24]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:24]=[C:23]([O:22][CH3:21])[C:3]=1[C:12]([O:13][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5867772-Fluoro-6-hydroxybenzoic acid

Product 1

HCID 2779314methyl 2-fluoro-6-methoxybenzoateYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-fluorosalicylic acid (5.00 g) in dimethylformamide (50 ml) was added anhydrous potassium carbonate (6.00 g) and methyl iodide (6.0 ml) with stirring at room temperature, then followed by vigorous stirring at room temperature for 12 hours. After the completion of the reaction, the reaction mixture was diluted by ether, washed with water and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure, to give the title compound (5.80 g, 98%) as an oil.

Workup

  1. stirringby vigorous stirring at room temperature for 12 hours
  2. customAfter the completion of the reaction
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-935de1b4a8f04f918dc13c7dd07bd8d3
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

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