Ethanol → Ethyl 3-Fluoro-4-nitrobenzoate

HRID 2068975Notes

Reaction equation

HRID 2068975 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH2:19][CH3:20])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 45036938Ethyl 3-Fluoro-4-nitrobenzoate

Procedure

To the liquid mixture of 3-fluoro-4-nitrobenzoic acid 9.71 g and ethanol 35 mL, conc. sulfuric acid 1.6 mL was added, followed by 16 hours' heating under reflux. After distilling the solvent off, water and tert-butyl methyl ether were added to the residue. The organic layer was extracted, washed with water and dried over magnesium sulfate. Distilling the solvent off, 7.40 g of the title compound was obtained.

Workup

  1. additionwas added
  2. temperature' heating
  3. temperatureunder reflux
  4. distillationAfter distilling the solvent off, water and tert-butyl methyl ether
  5. additionwere added to the residue
  6. extractionThe organic layer was extracted
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. distillationDistilling the solvent off, 7.40 g of the title compound
  10. customwas obtained

Sources & evidence

ORD record
ord-a660ccf88abc4c9f9aaa588f7f36cad7
Source dataset
uspto-grants-2012_10
Patent number
US08299080B2

Reaction notes

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