Nitric Acid → HCID 18695462, compound

HRID 1870216Notes

Reaction equation

HRID 1870216 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1.[N+:21]([O-])([OH:23])=[O:22]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:19]=[C:18]([F:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:3]=1[O:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 18695463HCID 18695463, compound

Product 1

HCID 18695462HCID 18695462, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In 16.ml of concentrated sulfuric acid, 3.29 g (11.8 mmol) of ethyl 4-(2,4-difluorophenoxy)benzoate was dissolved at the temperature not higher than 5° C. To the resulting mixture, 520 pl of fuming nitric acid was added at -5° C. or lower under stirring, followed by stirring for 30 minutes at the same temperature. The reaction mixture was poured into ice water and the insoluble matter so precipitated was collected by filtration. The resulting compound was dissolved in chloroform. The resulting solution was washed successively with water and brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (developing solvent: hexane:ethyl acetate=8:1) to give 2.42 g (63%) of ethyl 4-(2,4-difluoro-5-nitrophenoxy)benzoate.

Workup

  1. stirringby stirring for 30 minutes at the same temperature
  2. customthe insoluble matter so precipitated
  3. filtrationwas collected by filtration
  4. dissolutionThe resulting compound was dissolved in chloroform
  5. washThe resulting solution was washed successively with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by chromatography on a silica gel column (developing solvent: hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-b6fa3f335ba64842a906faaf458e5c9b
Source dataset
uspto-grants-2000_08
Patent number
US06096743

Reaction notes

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