Iodine → HCID 86610529, compound

HRID 495201Notes

Reaction equation

HRID 495201 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.II.FC(F)(F)C(O[I:37](C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.O>[CH3:14][O:13][CH2:12][O:11][C:9]1[C:8]([I:37])=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:6]([C:20](=[O:29])[C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:10]=1

Participants

7

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 68419954HCID 68419954, compound

Product 1

HCID 86610529HCID 86610529, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

Methyl 3,5-bis (methoxymethoxy)-2-(4-methoxybenzoyl)phenylacetate (0.75 g, 1.9 mmol) obtained in Example 134, Step 2 was dissolved in dichloromethane (20 mL). The resulting solution was cooled to −30° C., and iodine (0.47 g, 1.9 mmol) and [bis(trifluoroacetoxy)iodo]benzene (0.8 g, 1.9 mmol) were successively added thereto in an atmosphere of argon, followed by stirring for 2 hours. To the reaction mixture was added a saturated aqueous solution of sodium thiosulfate, and the mixture was further stirred for one hour, while the temperature was raised to room temperature. To the reaction mixture was added water for liquid separation, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting, residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/2) to obtain methyl 3,5-bis(methoxymethoxy)-2-iodo-6-(4-methoxybenzoyl)phenylacetate (0.95 g, 96%).

Workup

  1. stirringthe mixture was further stirred for one hour, while the temperature
  2. temperaturewas raised to room temperature
  3. customfor liquid separation
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting, residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/2)

Sources & evidence

ORD record
ord-5a9a22eb025f420f9bcd8d15d0edbf96
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

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