Methyl iodide → 5,7-Dichloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29389Notes

Reaction equation

HRID 29389 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[C:12]([OH:18])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].IC.[C:21]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[C:12]([O:18][CH3:21])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 687122235,7-Dichloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687124545,7-Dichloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid ethyl esterYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 120 mg of 5,7-dichloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester was added 1 mL of iodomethane, 200 mg 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 ethyl acetate solution was washed with brine. Removal of the solvent in vacuo gave 125 mg (99% yield) of 5,7-dichloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as off-white solid.

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate solution was washed with brine
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-3ef1fbba0152493389dc72a283a63524
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

Loading…