Potassium Iodide → HCID 67521261, compound

HRID 925256Notes

Reaction equation

HRID 925256 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[O:5].[C:13]([O-:16])(=[O:15])[CH3:14].[Na+].[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CC(O)=O.O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH2:3][CH2:2][O:16][C:13](=[O:15])[CH3:14])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 676722-Chloro-4'-fluoropropiophenoneHCID 517045Sodium Acetate

Product 1

HCID 67521261HCID 67521261, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3-chloro-1-(4-fluorophenyl)-propan-1-one (4.0 g, 21.5 mmol) in AcOH (30 ml) in a sealed tube are added sodium acetate (8.64 g, 105.4 mmol) and potassium iodide (0.36 g, 2.15 mmol) at RT. The reaction mixture is stirred at 130° C. for 16 h. After completion of reaction, the mixture is diluted with water (60 ml) and neutralized with aqueous sodium carbonate at 0° C. The aqueous layer is extracted with DCM (3×100 ml). The combined organic layers are washed with water (200 ml), brine (200 ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get the crude product, which is purified by column chromatography (silica gel, 10% EtOAc/hexane) to yield acetic acid [3-(4-fluorophenyl)-3-oxo-propyl]ester (3.00 g, 14.3 mmol, 66%).

Workup

  1. customAfter completion of reaction
  2. extractionThe aqueous layer is extracted with DCM (3×100 ml)
  3. washThe combined organic layers are washed with water (200 ml), brine (200 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customto get the crude product, which
  7. customis purified by column chromatography (silica gel, 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-8dac76b12081430f823e294f76df20d1
Source dataset
uspto-grants-2016_03
Patent number
US09284286B2

Reaction notes

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