Iodine → 2-IODO-5-METHOXYPHENOL

HRID 130657

Reaction equation

HRID 130657 reaction equation
[I:1]I.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1>C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[I:1][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][C:7]=1[OH:11]

Participants

5

Reactant 2

HCID 807IodineHCID 90073-Methoxyphenol

Product 1

HCID 114140152-IODO-5-METHOXYPHENOLYield 33.8%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolvent2×

Procedure

I2 (40.9 g, 161.1 mmol) was dissolved in CHCl3 (850 mL) with stirring over 1 hour. The solution was added slowly into a reaction mixture of 3-methoxyphenol 5-A (20 g, 161.1 mmol) and silver trifluoroacetate in 200 mL CHCl3 over 1.5 hours. The reaction was stirred at room temperature for 16 hours. Solids were removed by filtration. The filtrate was washed with 5% Na2S2O3(500 mL), saturated NaHCO3, brine, dried over MgSO4 and concentrated. The crude mixture was triturated with carbon tetrachloride to give 2-iodo-5-methoxyphenol 5-B (13.6 g) as a white solid. The remaining crude products were purified by silica gel column chromatography eluted with CH2Cl2to give 28.2 g of compound 5-B.

Workup

  1. stirringThe reaction was stirred at room temperature for 16 hours
  2. customSolids were removed by filtration
  3. washThe filtrate was washed with 5% Na2S2O3(500 mL), saturated NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude mixture was triturated with carbon tetrachloride

Sources & evidence

ORD record
ord-b48948d38dc0418fa826935f20fc0fa1
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Linked notes

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