Cesium carbonate → HCID 21930430, compound

HRID 1243713Notes

Reaction equation

HRID 1243713 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[OH:12][C:13]1[C:14]([O:21][CH3:22])=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:15]([CH:16]=[O:17])[C:14]=2[O:21][CH3:22])[CH:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 112753024-Chloro-2,5-difluorobenzonitrileHCID 118049533-Hydroxy-2-methoxybenzaldehyde

Product 1

HCID 21930430HCID 21930430, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2,5-difluorobenzonitrile (0.45 g, 2.6 mmol), 3-hydroxy-2-methoxybenzaldehyde (0.39 g, 2.6 mmol) and cesium carbonate (0.84 g, 2.6 mmol) were heated with stirring in dry DMF (5 mL) at 50° C. for 18 h. The reaction mixture was cooled, poured into 0.1N sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with 0.1N sodium hydroxide solution (1×), water (2×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo, and purified by chromatography to yield 4-chloro-5-fluoro-2-(3-formyl-2-methoxyphenoxy)benzonitrile (0.33 g, 42%) as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with 0.1N sodium hydroxide solution (1×), water (2×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo
  8. custompurified by chromatography

Sources & evidence

ORD record
ord-b4513056b7b145da83b3225f28f83510
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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