Dimethylformamide → 5-Nitro-2-(2,2,2-trifluoroethoxy)benzonitrile

HRID 1744527Notes

Reaction equation

HRID 1744527 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].[F:18][C:19]([F:23])([F:22])[CH2:20][OH:21].[H-].[Na+]>O>[N+:15]([C:12]1[CH:13]=[CH:14][C:7]([O:21][CH2:20][C:19]([F:23])([F:22])[F:18])=[C:8]([CH:11]=1)[C:9]#[N:10])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 130045665-Nitro-2-(2,2,2-trifluoroethoxy)benzonitrileYield 69.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylformamide solution (30 ml) containing 2-chloro-5-nitrobenzonitrile (10 g) and 2,2,2-trifluoroethanol (6 g) was added sodium hydride (60% content, 2.65 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 with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of toluene-diisopropyl ether to give 5-nitro-2-(2,2,2-trifluoroethoxy)benzonitrile (9.4 g), melting point: 94° C.

Workup

  1. temperaturecooling
  2. extractionextracted with toluene
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether was added to the residue
  7. customcrystallization
  8. customThe crystals were recrystallized from a mixed solvent of toluene-diisopropyl ether

Sources & evidence

ORD record
ord-fc1fee6e1a1042cb8a4f67a111ecc60d
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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