Potassium Carbonate → t-Butyl (3-iodophenoxy)acetate

HRID 1352867Notes

Reaction equation

HRID 1352867 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].S([O-])(O)(=O)=O.[K+]>CN(C)C=O>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 122723-IodophenolHCID 79177tert-Butyl bromoacetateHCID 516920Potassium bisulfate

Product 1

HCID 52449400t-Butyl (3-iodophenoxy)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of m-iodophenol (1.22 g, 5.55 mmol) in N,N-dimethylformamide (15 ml) were added potassium carbonate (1.40 g, 10.1 mmol) and t-butyl bromoacetate (1.22 ml, 6.25 mmol), and the mixture was stirred for 3 hours at 50° C. Thereto was added an aqueous 5% potassium hydrogensulfate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified with silica gel chromatography (hexane:ethyl acetate=4:1) to give the subject compound (1.85 g, 100%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified with silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-e1b41d7ca33e47caad642e24bc40dcae
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

Loading…