Cesium fluoride → HCID 59519383, compound

HRID 2102416Notes

Reaction equation

HRID 2102416 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9](Cl)[C:8]([Cl:13])=[C:7]([Cl:14])[N:6]=1)=[O:4].[F-:15].[Cs+]>CC#N.CCOC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9]([F:15])[C:8]([Cl:13])=[C:7]([Cl:14])[N:6]=1)=[O:4]

Participants

6

Reactant 2

HCID 25953Cesium fluorideHCID 676444Methyl 3,4,5,6-tetrachloropyridine-2-carboxylate

Product 1

HCID 59519383HCID 59519383, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4,5,6-tetrachloropyridine-2-carboxylic acid methyl ester (1.00 equivalent) in MeCN is added CsF (1.00 equivalent) at room temperature. The resulting mixture is refluxed with stirring for 16 hours. The reaction mixture is cooled to room temperature and diluted with EtOAc and water. The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product that is purified by flash column chromatography as necessary.

Workup

  1. temperatureThe resulting mixture is refluxed
  2. washThe organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d823a8fc9104659a5a1ed8909763bdb
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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