Potassium Fluoride → 2,4-Dinitro-5-fluorophenoxyacetonitrile

HRID 1381634Notes

Reaction equation

HRID 1381634 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11](Cl)=[CH:10][C:5]=1[O:6][CH2:7][C:8]#[N:9])([O-:3])=[O:2].[F-:18].[K+]>CS(C)=O>[N+:1]([C:4]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([F:18])=[CH:10][C:5]=1[O:6][CH2:7][C:8]#[N:9])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 14250577(5-Chloro-2,4-dinitrophenoxy)acetonitrile

Product 1

HCID 140535322,4-Dinitro-5-fluorophenoxyacetonitrileYield 89.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 2,4-dinitro-5-chlorophenoxyacetonitrile (5.0 g) and potassium fluoride (1.7 g) in dimethylsulfoxide (25 g) was stirred at 83° to 85° C. for 1 hour. The reaction mixture was poured into ice-water (300 ml) and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated. The precipitated crystals were collected by filtration and washed with ether to give crystalline 2,4-dinitro-5-fluorophenoxyacetonitrile (4.18 g; yield, 89.3%). M.P., 118°-118.5° C. (recrystallized from methanol).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-9e9df53f52724bdda0be8e41cc5f438a
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

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