p-Fluoronitrobenzene → Benzaldehyde, 4-methoxy-3-(4-nitrophenoxy)-

HRID 2427854Notes

Reaction equation

HRID 2427854 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[OH:11].C(=O)([O-])[O-].[Cs+].[Cs+].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[O:11][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 12127Isovanillin

Product 1

HCID 11108502Benzaldehyde, 4-methoxy-3-(4-nitrophenoxy)-Yield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methoxy-3-hydroxy-benzaldehyde (1.0 mg, 7.5 mmoles) is dissolved in DMF (20 mL). Cesium carbonate (2.45 g, 7.5 mmoles) and 1-fluoro-4-nitro-benzene (1.75 mL, 7.5 mmoles) are added and the resulting mixture is stirred at room temperature for 20 hours. The reaction mixture is then quenched by addition of 1N HCl and extracted with AcOEt. The organic layer is dried over Na2SO4 and the solvent is evaporated. The crude mixture is purified by chromatography on SiO2 (eluent:hexane:AcOEt=9:1) to yield 2.0 g of the pure title compound.

Workup

  1. customThe reaction mixture is then quenched by addition of 1N HCl
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer is dried over Na2SO4
  4. customthe solvent is evaporated
  5. customThe crude mixture is purified by chromatography on SiO2 (eluent:hexane:AcOEt=9:1)

Sources & evidence

ORD record
ord-40e694d1e7a14e4781ae377b08ab20ac
Source dataset
uspto-grants-2011_06
Patent number
US07968724B2

Reaction notes

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