Ethanol → Ethyl 4-fluoro-3-nitrobenzoate

HRID 2068278Notes

Reaction equation

HRID 2068278 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14](O)[CH3:15].C1(C)C=CC=CC=1.S(=O)(=O)(O)O>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:14][CH3:15])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1140TolueneHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 21277355Ethyl 4-fluoro-3-nitrobenzoateYield 93%

Procedure

4-Fluoro-3-nitrobenzoic acid (5.3 g, 0.029 mol), ethanol (15 mL, 0.26 mol), toluene (40 mL, 0.4 mol) and sulfuric acid (1.75 mL, 0.0328 mol) were added to a 100 mL round-bottomed flask fitted with a Dean Stark trap and reflux condenser. The reaction mixture was heated with stirring under nitrogen to reflux and maintained at reflux for 5 hours. The reaction mixture was concentrated to about half volume diluted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, water and dried over sodium sulfate. Concentration yielded a straw colored oil (5.68 g, 93%), which was used in the next step without further purification.

Workup

  1. customfitted with a Dean Stark trap
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. temperaturemaintained
  6. temperatureat reflux for 5 hours
  7. concentrationThe reaction mixture was concentrated to about half volume
  8. additiondiluted with ethyl acetate
  9. washThe organic layer was washed with saturated sodium bicarbonate, water
  10. dry with materialdried over sodium sulfate
  11. concentrationConcentration

Sources & evidence

ORD record
ord-451a7a94074b4fa988cc5d82507473b2
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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