Ethanol → Ethyl 4-fluoro-3-nitrobenzoate

HRID 1498887Notes

Reaction equation

HRID 1498887 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]>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

4

Reactant 2

HCID 702EthanolHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a suspension of 4-fluoro-3-nitrobenzoic acid (150 g, 0.810 mol) in ethanol (1000 ml), concentrated sulfuric acid (25 ml) was added dropwise, and the mixture was heated under reflux for 8 hours. After being allowed to cool, the mixture was concentrated under a reduced pressure, and water was added thereto under stirring. The precipitate was separated by filtration, washed with water and then subjected to through circulation drying to give the title compound (160 g, 93%) as a yellow solid.

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 8 hours
  4. temperatureto cool
  5. concentrationthe mixture was concentrated under a reduced pressure, and water
  6. additionwas added
  7. customThe precipitate was separated by filtration
  8. washwashed with water
  9. customdrying

Sources & evidence

ORD record
ord-f992553fb970473c9ac598378886bcce
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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