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

HRID 29399Notes

Reaction equation

HRID 29399 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Br: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]([Br: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 125429705-Bromo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687159755-Bromo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid ethyl esterYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 200 mg (0.67 mmol) of 5-bromo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester was added 0.5 mL of iodomethane, 200 mg of K2CO3 and 2 mL of DMF. The mixture was stirred at room temperature overnight. The mixture was washed with brine and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine. Removal of the solvent in vacuo gave 185 mg (88% yield) of 5-bromo-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 ethyl acetate layers were washed with brine
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-c40dd3f64f5d4e6bb18e4e6f9c268dd7
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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