Methyl iodide → 5-Iodo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29418Notes

Reaction equation

HRID 29418 reaction equation
[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([I:18])=[C:14]([OH:19])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].IC.[C:22]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([I:18])=[C:14]([O:19][CH3:22])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 687160405-Iodo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 687156165-Iodo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl esterYield 101.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 748 mg (2 mmol) of 5-iodo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester was added 1.42 g (10 mmol) of iodomethane, 553 mg (4 mmol) of K2CO3 and 10 mL of DMF. The mixture was stirred at room temperature overnight. The reaction mixture was washed with brine and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine. Removal of the solvent gave 790 mg (100% yield) of 5-iodo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester as a pale brown oil.

Workup

  1. washThe reaction 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

Sources & evidence

ORD record
ord-0caaa670807f47549ceaacc50ff704c3
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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