Water → HCID 22938669, compound

HRID 856637Notes

Reaction equation

HRID 856637 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8](C#N)[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-:19].[K+].[K+].O>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:19])[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 229385995-Chloro-α-(4-fluorophenyl)-2-pyridineacetonitrile

Product 1

HCID 22938669HCID 22938669, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Procedure

Under oxygen atmosphere, a mixed solution of 5-chloro-2-(α-cyano-4-fluorobenzyl)pyridine (16.14 g) and potassium carbonate (10.85 g) in DMSO-water (330-66 ml) was stirred at room temperature for 3 days. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 1:4), to give 5-chloro-2-(4-fluorobenzoyl)pyridine (14.37 g) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained residue was separated
  6. custompurified by column chromatography (ethyl acetate:hexane 1:4)

Sources & evidence

ORD record
ord-a285d92813444daabeb79f7593039d29
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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