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

HRID 2059618Notes

Reaction equation

HRID 2059618 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 triflouroacetate (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-4106534376434a52ad94b4d405db4cd1
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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