Water → t-Butyl (2-chloro-5-iodophenoxy)acetate

HRID 1352856Notes

Reaction equation

HRID 1352856 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[O:9][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 17144122-Chloro-5-iodophenol

Product 1

HCID 86594023t-Butyl (2-chloro-5-iodophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-iodophenol (509 mg, 2.00 mmol) in dimethylformamide were added potassium carbonate (415 mg, 3.00 mmol) and t-butyl bromoacetate (0.440 ml, 3.00 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 and purified with silica gel chromatography (hexane:ethyl acetate, 20:1) to give t-butyl (2-chloro-5-iodophenoxy)acetate (851 mg, quantitatively) as a colorless oil.

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
  5. custompurified with silica gel chromatography (hexane:ethyl acetate, 20:1)

Sources & evidence

ORD record
ord-c30250ea18c74c50a57b62eb4cac705d
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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