Hydrochloric Acid → 2,4-Dinitro-5-fluorophenoxyacetonitrile

HRID 1381637Notes

Reaction equation

HRID 1381637 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:15](#[N:18])[CH2:16][OH:17].C(=O)([O-])O.[Na+].Cl>O.CC(C)=O>[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:17][CH2:16][C:15]#[N:18])([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7857HydroxyacetonitrileHCID 675981,5-Difluoro-2,4-dinitrobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 140535322,4-Dinitro-5-fluorophenoxyacetonitrileYield 84.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a mixture of 1,5-difluoro-2,4-dinitrobenzene (2 g), acetone (20 g) and 50% aqueous glycolonitrile solution (1.2 g), a solution of sodium hydrogen carbonate (0.9 g) in water (18 g) was dropwise added at 27° to 30° C. in 5 minutes, and stirring was continued at 27° to 41° C. for 4.5 hours. After completion of the reaction, the reaction mixture was poured into 1% hydrochloric acid, extracted with ethyl acetate and concentrated. The precipitated crystals were collected by filtration and dried to give 2,4-dinitro-5-fluorophenoxyacetonitrile (2.0 g; yield, 83.0%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated
  4. filtrationThe precipitated crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-5d796cb6f8df43e4ac0ae35741b8825a
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

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