Water → 5-fluoro-7-iodo-6-methoxybenzofuran-3(2H)-one

HRID 1750007Notes

Reaction equation

HRID 1750007 reaction equation
[F:1][C:2]1[C:3]([OH:13])=[C:4]([I:12])[C:5]2[O:9][CH2:8][C:7](=[O:10])[C:6]=2[CH:11]=1.[C:14](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CN(C=O)C>[F:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([I:12])[C:5]2[O:9][CH2:8][C:7](=[O:10])[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 712785875-fluoro-6-hydroxy-7-iodobenzofuran-3(2H)-one

Product 1

HCID 712788015-fluoro-7-iodo-6-methoxybenzofuran-3(2H)-oneYield 23.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-fluoro-6-hydroxy-7-iodobenzofuran-3(2H)-one (0.256 g, 0.871 mmol) in DMF (5 mL) was added with potassium carbonate (0.110 g, 0.796 mmol). The mixture was added with dimethyl sulfate (0.0803 g, 0.637 mmol) at room temperature, and the mixture was stirred for 12 hours. The reaction mixture was added with water, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 5-fluoro-7-iodo-6-methoxybenzofuran-3(2H)-one (0.0582 g, 21%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-54f1f25a2bb7421493215ab53b3700f8
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…