Sodium Iodide → HCID 21995866, compound

HRID 1978723Notes

Reaction equation

HRID 1978723 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[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]=[CH:4][C:3]=1[O:8][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 27341841-(2-Bromoethoxy)propane

Product 1

HCID 21995866HCID 21995866, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In DMF (120 ml) was dissolved 2-bromophenol (12 g), and to the solution were added potassium carbonate (14.4 g) and sodium iodide (10.4 g). To the mixture was added 2-bromoethylpropylether (10.4 ml), and the mixture was stirred at 90° C. for 16 hours. The reaction 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-2-(2-propoxyethoxy)benzene (14.4 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-2389317e888a452fad20d5d8933e7411
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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