Water → 4-Chloro-2-(4-formyl-2-methoxy-phenoxy)-benzonitrile

HRID 1178467Notes

Reaction equation

HRID 1178467 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[O:11]=[CH:12][C:13]1[CH:21]=[CH:20][C:18]([OH:19])=[C:15]([O:16][CH3:17])[CH:14]=1.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:19][C:18]2[CH:20]=[CH:21][C:13]([CH:12]=[O:11])=[CH:14][C:15]=2[O:16][CH3:17])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 10796Cesium carbonateHCID 936554-Chloro-2-fluorobenzonitrile

Product 1

HCID 219303704-Chloro-2-(4-formyl-2-methoxy-phenoxy)-benzonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-fluorobenzonitrile (0.60 g, 3.9 mmol), vanillin (0.59 g, 3.9 mmol) and cesium carbonate (1.26 g, 3.9 mmol) were heated with stirring in dry DMF (4 ml) at 50° C. for 22 h. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with water, 10% aqueous sodium carbonate (2×), water (2×), brine, and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 4-chloro-2-(4-formyl-2-methoxy-phenoxy)-benzonitrile (0.98 g, 88%) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with water, 10% aqueous sodium carbonate (2×), water (2×), brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-776c71831f1f4206801b4feadb5ddb84
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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