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

HRID 1381639Notes

Reaction equation

HRID 1381639 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+]>CN(C)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 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
122 °C

Procedure

A suspension of ethyl 2,4-dinitro-5-chlorophenoxyacetate (2.0 g) and potassium fluoride (0.76 g) in N,N-dimethylformamide (10 g) was stirred at a temperature of 122° C. for 1.5 hours. 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 (1.4 g; yield, 74.0%).

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-37640bf011034ffb8b774cd03d64c4f9
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

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