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

HRID 1978632Notes

Reaction equation

HRID 1978632 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH3:24]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH3:24])=[C:4]([Cl:9])[CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 198594-Bromo-2-chlorophenolHCID 1235061-(2-Chloroethoxy)propane

Product 1

HCID 219956844-Bromo-2-chloro-1-(2-propoxyethoxy)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-bromo-2-chlorophenol (10 g) in DMF (200 ml) were added at room temperature potassium carbonate (9.99 g), sodium iodide (7.95 g) and 2-chloroethylpropylether (6.7 ml), and the mixture was stirred at 90° C. for 24 hours. To the mixture was added water, and the mixture was extracted with hexane. The organic layer was washed with water, 1N sodium hydroxide solution and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give pale yellow oil of 4-bromo-2-chloro-1-(2-propoxyethoxy)benzene (14.91 g).

Workup

  1. extractionthe mixture was extracted with hexane
  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

Sources & evidence

ORD record
ord-3e6702724b0d479692c3047928c7e0f3
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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