Water → 2,4-Dinitro-5-fluorophenoxyacetonitrile

HRID 1381636Notes

Reaction equation

HRID 1381636 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].[C:21](#[N:24])[CH2:22][OH:23].O>C(#N)C>[N+:12]([C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[C:6]([F:8])=[CH:7][C:2]=1[O:23][CH2:22][C:21]#[N:24])([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 7857HydroxyacetonitrileHCID 11430Potassium CarbonateHCID 675981,5-Difluoro-2,4-dinitrobenzene

Product 1

HCID 140535322,4-Dinitro-5-fluorophenoxyacetonitrileYield 89.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 1,5-difluoro-2,4-dinitrobenzene (3.8 g) and anhydrous potassium carbonate (3.1 g) in acetonitrile (50 ml) kept at room temperature, a solution of glycolonitrile (1.5 g) in acetonitrile (10 ml) was dropwise added, followed by stirring at room temperature for 1 hour. The reaction mixture was heated and allowed to reflux for 30 minutes (inner temperature, 83° C.). After cooling, the resultant mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and concentrated to give crystalline 2,4-dinitro-5-fluorophenoxyacetonitrile (4.0 g; yield, 89.1%).

Workup

  1. customkept at room temperature
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 30 minutes (inner temperature, 83° C.)
  4. temperatureAfter cooling
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9b696c793642422090dbeb8b626bda29
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

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