Iodine → HCID 66733550, compound

HRID 403011

Reaction equation

HRID 403011 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:25]I>C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:14]([I:25])=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][OH:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 743383,4-Bis(benzyloxy)benzyl alcohol

Product 1

HCID 66733550HCID 66733550, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolvent2×

Procedure

The dibenzyloxybenzyl alcohol 28 (21.44 mmol) and silver trifluoroacetate (21.44 mmol) were suspended in 100 mL of dry chloroform and stirred under argon. A solution of iodine (21.44 mmol) in dry chloroform (50 mL) was added to the suspension dropwise at room temperature. The reaction mixture was then stirred for a further period of 2 h and filtered. The filtrate was washed with 20% sodium thiosulfate solution in water. The organic layer was separated and dried over anhydrous Na2SO4. Filtration was followed by evaporation of the chloroform solution resulting in the pure iodo compound, 3,4-Dibenzyloxy-6-iodobenzyl alcohol (29), as a pale yellow solid in 84% yield.

Workup

  1. stirringThe reaction mixture was then stirred for a further period of 2 h
  2. filtrationfiltered
  3. washThe filtrate was washed with 20% sodium thiosulfate solution in water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationFiltration
  7. customwas followed by evaporation of the chloroform solution

Sources & evidence

ORD record
ord-ecb27ec953764accb3730e698a8568d6
Source dataset
uspto-grants-2014_06
Patent number
US08742139B2

Linked notes

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