Water → HCID 21930378, compound

HRID 1178465Notes

Reaction equation

HRID 1178465 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.O[C:12]1[C:13]([O:20][CH3:21])=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16].C(=O)([O-])[O-:23].[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:23][C:18]2[CH:19]=[CH:12][C:13]([O:20][CH3:21])=[C:14]([CH:15]=[O:16])[CH:17]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 936554-Chloro-2-fluorobenzonitrileHCID 118049533-Hydroxy-2-methoxybenzaldehyde

Product 1

HCID 21930378HCID 21930378, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-fluorobenzonitrile (0.65 g, 4.2 mmol), 3-hydroxy-2-methoxybenzaldehyde (0.64 g, 4.2 mmol) and cesium carbonate (1.37 g, 4.2 mmol) were heated with stirring in dry DMF (4 ml) at 50° C. for 18 h. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with water (2×), 10% aqueous sodium carbonate (2×), water and brine and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 4-chloro-2-(3-formyl-4-methoxy-phenoxy)-benzonitrile (1.09 g, 90%) as a yellow-orange solid.

Workup

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

Sources & evidence

ORD record
ord-3477ef0c144b439bbaf65f3d9e611419
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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