Iodine → 3-Acetoxy-2,4-dimethoxy-iodobenzene

HRID 1042582Notes

Reaction equation

HRID 1042582 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[O:11][C:12](=[O:14])[CH3:13].[I:15]I>C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[C:12]([O:11][C:4]1[C:3]([O:2][CH3:1])=[C:8]([I:15])[CH:7]=[CH:6][C:5]=1[O:9][CH3:10])(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 807IodineHCID 2555872,6-Dimethoxyphenol acetate

Product 1

HCID 574219533-Acetoxy-2,4-dimethoxy-iodobenzeneYield 96%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolvent

Procedure

To an ice-cooled suspension of acetic acid 2,6-dimethoxy-phenyl ester (1.0 g, 5.1 mmol) and silver trifluoroacetate (5.1 mmol) in CHCl3 (16 ml) was added iodine (1.3 g, 5.1 mmol) and the reaction stirred for 1 hour. The crude mixture was filtered through celite to remove the precipitated silver iodide and the filtrate was washed with 10% Na2S2O3 (aq). An emulsion was formed and the mixture was again passed through celite and the filtrate washed with brine, dried over MgSO4 and concentrated under reduced pressure to give the product as a tan solid (1.57 g, 96%). 1H-NMR (300 MHz, CDCl3) δ 7.55 (d, J=8.9 Hz, 1H), 6.54 (d, J=8.9 Hz, 1H), 3.80 (s, 6H), 2.33 (s, 3H).

Workup

  1. filtrationThe crude mixture was filtered through celite
  2. customto remove the precipitated silver iodide
  3. washthe filtrate was washed with 10% Na2S2O3 (aq)
  4. customAn emulsion was formed
  5. washthe filtrate washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-df8bb08299344855b54b0295e0d44957
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

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