Potassium Iodide → HCID 12531868, compound

HRID 1863328Notes

Reaction equation

HRID 1863328 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([OH:9])=[CH:7][CH:8]=1.C[O-].[Na+].[I-].[K+].Br[CH:18]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]>CO.C1C=CC=CC=1.O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([O:9][CH:18]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)=[CH:25][CH:24]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 678744-(Trifluoromethyl)phenolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531868HCID 12531868, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4.08 g of α,α,α-trifluoro-p-cresol, 1.19 g of sodium methoxide and 50 mg of potassium iodide in 40 ml of methanol is added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture is refluxed overnight and then poured into 100 ml of water. The mixture is then extracted with 2×75 ml of ether. The combined extracts are washed with 2×50 ml of 5% NaOH, 50 ml of water, 50 ml of saturated brine and dried (MgSO4). Evaporation of the solvent yields a yellow oil. Chromatography on 100 g of silica gel (benzene, 400 ml) affords the product as a colorless oil.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. extractionThe mixture is then extracted with 2×75 ml of ether
  3. washThe combined extracts are washed with 2×50 ml of 5% NaOH, 50 ml of water, 50 ml of saturated brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customyields a yellow oil

Sources & evidence

ORD record
ord-9a55e18df14346e287e19b6397ea1702
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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