Potassium Fluoride → Ethyl 2,4-dinitro-5-fluorophenoxyacetate

HRID 1381638Notes

Reaction equation

HRID 1381638 reaction equation
[N+:1]([C:4]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14](Cl)=[CH:13][C:5]=1[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])([O-:3])=[O:2].[F-:21].[K+]>CS(C)=O>[N+:1]([C:4]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]([F:21])=[CH:13][C:5]=1[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 14423666Ethyl 2,4-dinitro-5-chlorophenoxyacetate

Product 1

HCID 14423667Ethyl 2,4-dinitro-5-fluorophenoxyacetateYield 89.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of ethyl 2,4-dinitro-5-chlorophenoxyacetate (2.0 g) and potassium fluoride (0.57 g) in dimethylsulfoxide (10 g) was stirred at a temperature of 90° to 101° C. After cooling, the reaction mixture was diluted with ice water (200 ml) and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution in order, dried over anhydrous magnesium sulfate and concentrated to give ethyl 2,4-dinitro-5-fluorophenoxyacetate (1.7 g; yield, 89.9%). M.P., 59.0°-59.5° C. (recrystallized from methanol).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride solution in order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-92638170583e419bb896ed2c781b35c7
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

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