Cesium carbonate → 3-Fluoro-2-(3-formyl-2-methoxyphenoxy)-4-methylbenzonitrile

HRID 1243722Notes

Reaction equation

HRID 1243722 reaction equation
F[C:2]1[C:9]([F:10])=[C:8]([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>[F:10][C:9]1[C:2]([O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:15]([CH:16]=[O:17])[C:14]=2[O:21][CH3:22])=[C:3]([CH:6]=[CH:7][C:8]=1[CH3:11])[C:4]#[N:5]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 118049533-Hydroxy-2-methoxybenzaldehydeHCID 177506922,3-Difluoro-4-methylbenzonitrile

Product 1

HCID 219304453-Fluoro-2-(3-formyl-2-methoxyphenoxy)-4-methylbenzonitrileYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Difluoro-4-methylbenzonitrile (0.21 g, 1.4 mmol), 3-hydroxy-2-methoxybenzaldehyde (0.21 g, 1.4 mmol) and cesium carbonate (0.45 g, 1.4 mmol) were heated with stirring in dry DMF (4 mL) at 50° C. for 18 h. The reaction mixture was cooled, poured into 0.1N sodium hydroxide-solution and extracted with diethyl ether. The ether layer was separated, washed with 0.1N sodium hydroxide solution (2×), water (3×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo, and purified by chromatography to yield 3-fluoro-2-(3-formyl-2-methoxyphenoxy)-4-methylbenzonitrile (0.12 g, 31%) as a colourless glass.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with diethyl ether
  3. customThe ether layer was separated
  4. washwashed with 0.1N sodium hydroxide solution (2×), water (3×), 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-f8c49107ca374087829d623d81910357
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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