Sodium Iodide → HCID 21995975, compound

HRID 1978708Notes

Reaction equation

HRID 1978708 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=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][C:5]([S:8][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH3:23])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 1235061-(2-Chloroethoxy)propane

Product 1

HCID 21995975HCID 21995975, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In DMF (96 ml) was dissolved 4-bromobenzenethiol (12 g). To the mixture were added dropwise at room temperature potassium carbonate (12.3 g) and sodium iodide (10.5 g) and then was added dropwise 2-chloroethylpropylether (9.6 ml), and the mixture was stirred at 90° C. for 14 hours and cooled to room temperature. 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=10/1) to give 1-bromo-4-(2-propoxyethylthio)benzene (16.9 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 evaporated
  6. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-8e163da3b0a948508728eab18f52a449
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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