Sodium Iodide → HCID 21995835, compound

HRID 1978717Notes

Reaction equation

HRID 1978717 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH3:23]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH3:23])[CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 1235061-(2-Chloroethoxy)propane

Product 1

HCID 21995835HCID 21995835, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In DMF (140 ml) was dissolved 3-bromophenol (14 g). To the mixture were added potassium carbonate (15.7 g) and sodium iodide (12.1 g) and then was added 2-chloroethylpropylether (12.3 ml), and the mixture was stirred at 90° C. for 18 hours. There action mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=12/1) to give 1-bromo-3-(2-propoxyethoxy)benzene (11.1 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. customUnder reduced pressure, the solvent was evaporated
  5. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=12/1)

Sources & evidence

ORD record
ord-520aa223997641eebbf6ea6f6a1fa1cf
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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