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

HRID 1178504Notes

Reaction equation

HRID 1178504 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-d4e827f357b24cc1a11f0717c612bf34
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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