Phenol → Benzonitrile, 5-nitro-2-phenoxy-

HRID 1744522Notes

Reaction equation

HRID 1744522 reaction equation
CN(C)C=O.Cl[C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=1[C:9]#[N:10].[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+]>O>[N+:15]([C:12]1[CH:13]=[CH:14][C:7]([O:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]([CH:11]=1)[C:9]#[N:10])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 514846Benzonitrile, 5-nitro-2-phenoxy-Yield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylformamide solution (30 ml) containing 2-chloro-5-nitrobenzonitrile (10 g) and phenol (5.7 g) was added sodium hydride (60% content, 2.63 g) under ice-cooling, and the mixture was stirred for 1 h. The reaction mixture was added to water and extracted with toluene. The organic layer was washed saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether to give 5-nitro-2-phenoxybenzonitrile (10.8 g), melting point: 126° C.

Workup

  1. temperaturecooling
  2. extractionextracted with toluene
  3. washThe organic layer was washed saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customafter which the solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-15ab108e11b94d43a7834058796b23a7
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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