Cesium carbonate → 2-(3-Formyl-2-methoxy-phenoxy)4-methoxy-benzonitrile

HRID 1243720Notes

Reaction equation

HRID 1243720 reaction equation
F[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[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>[CH:16]([C:15]1[C:14]([O:21][CH3:22])=[C:13]([CH:20]=[CH:19][CH:18]=1)[O:12][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])=[O:17]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 6398782-Fluoro-4-methoxybenzonitrileHCID 118049533-Hydroxy-2-methoxybenzaldehyde

Product 1

HCID 219303802-(3-Formyl-2-methoxy-phenoxy)4-methoxy-benzonitrileYield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-4-methoxy-benzonitrile (0.28 g, 1.8 mmol), 3-hydroxy-2-methoxybenzaldehyde (0.28 g, 1.8 mmol) and cesium carbonate (0.90 g, 2.4 mmol) were heated with stirring in dry DMF (4 mL) at 50° C. for 40 h. The reaction mixture was cooled, poured into 1N sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with 1N sodium hydroxide solution (4×), water (4×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 2-(3-formyl-2-methoxy-phenoxy)4-methoxy-benzonitrile (0.38 g, 73%) as a tan oil.

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 (4×), water (4×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-75f5396988f4493b87e605d8e5b85e90
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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