Methyl iodide → Tert-butyl 5-bromo-4-methoxy-3-methyl-benzofuran-2-carboxylate

HRID 29394Notes

Reaction equation

HRID 29394 reaction equation
[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([Br: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]([Br: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 687139965-Bromo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 68714104Tert-butyl 5-bromo-4-methoxy-3-methyl-benzofuran-2-carboxylateYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 220 mg (0.67 mmol) of 5-bromo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester was added 0.42 mL (6.7 mmol) of iodomethane, 185 mg (1.34 mmol) of K2CO3 and 2 mL of DMF. The mixture was stirred at room temperature over night. The mixture was washed with brine and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine. Removal of the solvent gave 230 mg (100% yield) of 5-bromo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester as a colorless oil.

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

Sources & evidence

ORD record
ord-3ea2a0236ed64ff6a11aa0f9a89ebdcc
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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