Ethanol → Ethyl 2-fluoro-5-nitrobenzoate

HRID 1593064Notes

Reaction equation

HRID 1593064 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>C(OCC)(=O)C>[CH2:19]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[F:1])[CH3:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2809972-Fluoro-5-nitrobenzoic acid

Product 1

HCID 12793176Ethyl 2-fluoro-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-fluoro-5-nitro-benzoic acid (0.269 g, 1.45 mmol) in 3 mL ethanol, was added concentrated sulfuric acid (0.5 ml). The solution was refluxed under argon for 3 hours. The mixture was stirred at room temperature for 2 hours, then diluted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, concentrated in vacuo to give pure 2-fluoro-5-nitro-benzoic acid ethyl ester.

Workup

  1. temperatureThe solution was refluxed under argon for 3 hours
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7346ff850514955a1f80547d3ff8978
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

Loading…