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

HRID 984175Notes

Reaction equation

HRID 984175 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 mL). 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-8b808a59bb5e420ebd51c8a1e2821e7f
Source dataset
uspto-grants-2005_03
Patent number
US06867221B2

Reaction notes

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