Sodium Iodide → HCID 21995970, compound

HRID 1978753Notes

Reaction equation

HRID 1978753 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].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])=[CH:4][C:3]=1[Cl:9]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1235061-(2-Chloroethoxy)propaneHCID 70181824-Bromo-3-chlorophenol

Product 1

HCID 21995970HCID 21995970, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In DMF (98 ml) was dissolved 4-bromo-3-chlorophenol (9.8 g), and to the solution were added at room temperature potassium carbonate (9.8 g), sodium iodide (7.8 g) and 2-chloroethylpropylether (7.8 ml). The mixture was stirred at 90° C. for 16 hours, cooled to room temperature, poured into water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was removed, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1) to give 1-bromo-2-chloro-4-(2-propoxyethoxy)benzene (8.8 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customUnder reduced pressure, the solvent was removed
  6. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-979b564eeea84133879a269fc67be547
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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