Water → t-Butyl (3-iodophenoxy)acetate

HRID 1352862Notes

Reaction equation

HRID 1352862 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].O>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 962WaterHCID 11430Potassium CarbonateHCID 122723-IodophenolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 52449400t-Butyl (3-iodophenoxy)acetateYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodophenol (2.20 g, 10.0 mmol) in dimethylformamide (20 ml) were added potassium carbonate (2.07 g, 15.0 mmol) and t-butyl bromoacetate (1.62 ml, 11.0 mmol), and the mixture was stirred for 1 hour at room temperature. Thereto was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% aqueous citric acid solution, water, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order, and dried over magnesium sulfate. The solvent was removed to give the subject compound as a colorless oil (3.28 g, 98%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 10% aqueous citric acid solution, water
  3. dry with materialan aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order, and dried over magnesium sulfate
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-bb475fc85c2b407fb364999f0dd3d60a
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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