Sodium Iodide → HCID 21995783, compound

HRID 1978706Notes

Reaction equation

HRID 1978706 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[Cl:17][C:18]1[S:19][C:20]([CH2:23]Cl)=[CH:21][CH:22]=1>CN(C=O)C.O>[Cl:17][C:18]1[S:19][C:20]([CH2:23][O:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 5830792-Chloro-5-(chloromethyl)thiophene

Product 1

HCID 21995783HCID 21995783, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In DMF (75 ml) was dissolved 4-bromophenol (7.5 g). To the mixture were added at room temperature potassium carbonate (7.2 g) and sodium iodide (6.5 g) and then was added dropwise 2-chloro-5-chloromethyl thiophene (6.5 g), and the mixture was stirred at 90° C. for 6 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 4-bromophenyl (5-chloro-2-thienyl)methyl ether (8.2 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-04dd0055bf9d4b9987f0359f963ba56f
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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