Water → 4-Chloro-2-(2-ethoxy-3-formylphenoxy)benzonitrile

HRID 1243693Notes

Reaction equation

HRID 1243693 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[CH2:11]([O:13][C:14]1[C:21]([OH:22])=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=[O:17])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:22][C:21]2[CH:20]=[CH:19][CH:18]=[C:15]([CH:16]=[O:17])[C:14]=2[O:13][CH2:11][CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 936554-Chloro-2-fluorobenzonitrileHCID 106786312-Ethoxy-3-hydroxybenzaldehyde

Product 1

HCID 219303824-Chloro-2-(2-ethoxy-3-formylphenoxy)benzonitrileYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-fluorobenzonitrile (0.35 g, 2.2 mmol), 2-ethoxy-3-hydroxybenzaldehyde (0.37 g, 2.2 mmol) and cesium carbonate (0.73 g, 2.2 mmol) were heated with stirring in dry DMF (4 mL) at 50° C. for 19 h. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with 1N sodium hydroxide solution (2×), water (2×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 4-chloro-2-(2-ethoxy-3-formylphenoxy)benzonitrile (0.55 g, 82%) as a tan solid.

Workup

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

Sources & evidence

ORD record
ord-76bfe85e2de746a7ab9d7db8380ab3ae
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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