Potassium Iodide → HCID 15381110, compound

HRID 1107508Notes

Reaction equation

HRID 1107508 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH:18]([CH3:22])[C:19](=[O:21])[CH3:20]>O.CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH:18]([CH3:22])[C:19](=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 200263-Chloro-2-butanone

Product 1

HCID 15381110HCID 15381110, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

60 g (347 mmol) of 2-bromophenol, 57.43 g (416 mmol) of potassium carbonate, 57 g (347 mmol) of potassium iodide, 600 ml of N,N-dimethylformamide and 4.34 g (416 mmol) of 3-chloro-2-butanone are introduced into a 1 liter three-necked flask equipped with a reflux condenser. The mixture is heated at 80° C. for 16 hours. 1500 ml of water are added and extraction is then carried out with ethyl acetate (3×400 ml). The organic phases are combined, washed with a molar sodium hydroxide solution (2×500 ml), dried over magnesium sulphate and concentrated. The residue is purified by chromatography on a silica column (elution solvent cyclohexane:ethyl acetate 9:1). 75.07 g (Yield: 89%) of 3-(2-bromophenoxy)-2-butanone (yellow oil) are obtained.

Workup

  1. customequipped with a reflux condenser
  2. extractionextraction
  3. washwashed with a molar sodium hydroxide solution (2×500 ml)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography on a silica column (elution solvent cyclohexane:ethyl acetate 9:1)

Sources & evidence

ORD record
ord-d09bc3a8c04440ce9b383930b56754a1
Source dataset
uspto-grants-2000_05
Patent number
US06060508

Reaction notes

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