Isopropyl iodide → 1,3-Dimethoxy-5-iodo-2-isopropoxybenzene

HRID 395447Notes

Reaction equation

HRID 395447 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([I:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[CH:19](I)([CH3:21])[CH3:20]>CN(C=O)C>[CH3:11][O:10][C:5]1[CH:6]=[C:7]([I:9])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[O:12][CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 224855374-Iodo-2,6-dimethoxyphenol

Product 1

HCID 225579361,3-Dimethoxy-5-iodo-2-isopropoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 2,6-dimethoxy-4-iodophenol (1.0 g) and potassium carbonate (938 mg) in DMF (10 mL) was added isopropyl iodide (507 □L). The mixture was stirred at 60° C. for 3 hours and evaporated. Ethyl acetate and water were added to the residue, the organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was applied to a column of silica gel using hexane-ethyl acetate (5:1) as an eluent to give the title compound.

Workup

  1. customevaporated
  2. additionEthyl acetate and water were added to the residue
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-f1f23f5b2bb148b4880ab8dfa774f03d
Source dataset
uspto-grants-2003_08
Patent number
US06605620B1

Reaction notes

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