Potassium Iodide → HCID 23157690, compound

HRID 273384

Reaction equation

HRID 273384 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:19]([O:21][CH2:22][CH2:23]Cl)[CH3:20]>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:20][CH2:19][O:21][CH2:22][CH3:23])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 23157690HCID 23157690, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (12 g, 59.7 mmol), potassium iodide (1.5 g, 9.0 mmol) and potassium carbonate (9.9 g, 71.6 mmol) in N,N-dimethylformamide (80 mL) was added 2-chloroethyl ethyl ether (9.7 g, 89.3 mmol) at room temperature with stirring and the mixture was stirred at 70° C. for 2 days. The reaction mixture was cooled and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=19/1) to give the title compound (15.9 g, yield 98%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at 70° C. for 2 days
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=19/1)

Sources & evidence

ORD record
ord-d36509fef7d647219d495960856c54a5
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Linked notes

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