Iodine → Methyl 2-ethyl-6-iodo-3,5-bis(methoxymethoxy)phenylacetate

HRID 495294Notes

Reaction equation

HRID 495294 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][CH2:10][O:11][CH3:12])=[CH:7][C:6]([O:13][CH2:14][O:15][CH3:16])=[CH:5][C:4]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH3:2].II.FC(F)(F)C(O[I:29](C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[C:8]([O:9][CH2:10][O:11][CH3:12])=[CH:7][C:6]([O:13][CH2:14][O:15][CH3:16])=[C:5]([I:29])[C:4]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH3:2]

Participants

7

Reactant 5

HCID 807IodineHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 23116468Methyl 2-ethyl-3,5-bis(methoxymethoxy)phenylacetate

Product 1

HCID 86613501Methyl 2-ethyl-6-iodo-3,5-bis(methoxymethoxy)phenylacetateYield 54.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-30 °C

Procedure

Methyl 2-ethyl-3,5-bis(methoxymethoxy)phenylacetate (300 mg, 1.0 mmol) was dissolved in chloroform (9.0 mL), and with stirring at −30° C., iodine (260 mg, 1.0 mmol) and [bis(trifluoroacetoxy)iodo]benzene (440 mg, 1.0 mmol) were added thereto in order, and stirred at the same temperature for 1 hour. Aqueous saturated sodium thiosulfate solution and aqueous saturated sodium hydroxide solution were added to the reaction mixture, then heated up to room temperature, and stirred further for 2 hours. The reaction mixture was subjected to liquid-liquid separation, and the aqueous layer was washed twice with ethyl acetate. The organic layers were combined and washed with aqueous saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/9 to 1/4) to obtain methyl 2-ethyl-6-iodo-3,5-bis(methoxymethoxy)phenylacetate (230 mg, 53%).

Workup

  1. stirringin order, and stirred at the same temperature for 1 hour
  2. temperatureheated up to room temperature
  3. stirringstirred further for 2 hours
  4. customThe reaction mixture was subjected to liquid-liquid separation
  5. washthe aqueous layer was washed twice with ethyl acetate
  6. washwashed with aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated away under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/9 to 1/4)

Sources & evidence

ORD record
ord-84cf24afdc65456ea65acd9e549b6a89
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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