Sodium Iodide → 4-Bromo-2-ethoxy-1-(2-propoxyethoxy)benzene

HRID 1978631Notes

Reaction equation

HRID 1978631 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH2:10][CH3:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:21][CH2:22][O:23][CH2:24][CH2:25][CH3:26]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:21][CH2:22][O:23][CH2:24][CH2:25][CH3:26])=[C:4]([O:9][CH2:10][CH3:11])[CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1235061-(2-Chloroethoxy)propaneHCID 218775414-Bromo-2-ethoxyphenol

Product 1

HCID 219957524-Bromo-2-ethoxy-1-(2-propoxyethoxy)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-bromo-2-ethoxyphenol (8.0 g) in DMF (50 ml) were added at room temperature potassium carbonate (7.65 g), sodium iodide (6.64 g) and 2-chloroethylpropylether (5.6 ml), and the mixture was stirred at 90° C. for 24 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 1N sodium hydroxide solution and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:4) to give yellow oil of 4-bromo-2-ethoxy-1-(2-propoxyethoxy)benzene (10.33 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, 1N sodium hydroxide solution and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:4)

Sources & evidence

ORD record
ord-1fee594bbf004a70a6236c68f3c76724
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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