Methyl iodide → 5-Chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29384Notes

Reaction equation

HRID 29384 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([OH:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].IC.[C:20]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:20])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 687146975-Chloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687120345-Chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid ethyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-chloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (120 mg, 0.47 mmol) was added 0.3 mL (4.7 mmol) of iodomethane, 130 mg (2 eq) of K2CO3 and 4 mL of DMF. The mixture was stirred at room temperature overnight. The mixture was washed with brine and extracted with ethyl acetate. The combined organic solution was washed with brine and water. Removal of the solvent in vacuo gavel 19 mg (94% yield) of 5-chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as a white solid.

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. washThe combined organic solution was washed with brine and water

Sources & evidence

ORD record
ord-ca8c8c18006a4cc6a15b6364c4e26db5
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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