Sulfuric Acid → Ethyl 2-ethoxy-4-fluoro-5-nitrobenzoate

HRID 2068973Notes

Reaction equation

HRID 2068973 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].S(=O)(=O)(O)O.[N+:21]([O-])([O-:23])=[O:22].[K+]>>[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([F:15])[C:12]([N+:21]([O-:23])=[O:22])=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 59198761Ethyl 2-ethoxy-4-fluorobenzoate

Product 1

HCID 59198570Ethyl 2-ethoxy-4-fluoro-5-nitrobenzoate

Procedure

In nitrogen atmosphere, to ethyl 2-ethoxy-4-fluorobenzoate as synthesized in above Production Example 31, 6.51 g, conc. sulfuric acid 34 mL was added under cooling with ice. Potassium nitrate 3.26 g was further added little by little, under cooling with salt-ice, followed by stirring for 3.4 hours under cooling with ice. The reaction liquid was poured in ice water, and the precipitated crystals were recovered by filtration and washed with water. Recrystallizing the crystals from tert-butyl methyl ether-hexane mixed solvent, 4.49 g of the title compound was obtained.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. temperatureunder cooling with ice
  4. customThe reaction liquid
  5. filtrationthe precipitated crystals were recovered by filtration
  6. washwashed with water
  7. customRecrystallizing the crystals from tert-butyl methyl ether-hexane mixed solvent

Sources & evidence

ORD record
ord-29c05b43c387439bac860355d0eb6c83
Source dataset
uspto-grants-2012_10
Patent number
US08299080B2

Reaction notes

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