Dimethylformamide → 4-(4-methoxyphenoxy)benzonitrile

HRID 2269711Notes

Reaction equation

HRID 2269711 reaction equation
[H-].[Na+].CN(C=O)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.F[C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1>O>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 90154-MethoxyphenolHCID 145174-FluorobenzonitrileHCID 24758Sodium hydride

Product 1

HCID 14902794-(4-methoxyphenoxy)benzonitrileYield 45.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% dispersion in oil; 0.8 g) was added to a DMF (20 ml) solution of 4-methoxyphenol (2.4 g). The reaction mixture was stirred at room temperature for 5 minutes, to which was added 4-fluorobenzenecarbonitrile (2.4 g). The reaction mixture was stirred at room temperature for 4 hours, which was further stirred at 50° C. for one hour. The reaction mixture was poured into water, which was extracted with toluene. The organic layer was washed with water, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1), and then recrystallized from toluene-hexane to obtain 4-[(4-methoxyphenyl)oxy]benzenecarbonitrile (2.0 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 hours
  2. stirringwhich was further stirred at 50° C. for one hour
  3. extractionwas extracted with toluene
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)
  8. customrecrystallized from toluene-hexane

Sources & evidence

ORD record
ord-33f889de817e4425b775641964a9ad12
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

Loading…