Ethanol → Ethyl 2-fluoro-4-nitrobenzoate

HRID 2235088Notes

Reaction equation

HRID 2235088 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[CH2:19]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=1[F:1])[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 3026792-Fluoro-4-nitrobenzoic acid

Product 1

HCID 10727300Ethyl 2-fluoro-4-nitrobenzoateYield 65%

Procedure

A solution of 2-fluoro-4-nitro-benzoic acid (1.0 g, 5.4 mmol) in ethanol (10 ml) was treated with concentrated sulphuric acid (0.3 ml) and stirred at reflux overnight. Upon cooling to room temperature, a crystalline precipitate started to form. Precipitation was completed at 0° C., the solid was filtered, washing with ethanol/water 2:1, and dried under high vacuum, yielding 750 mg (65% yield) 2-fluoro-4-nitro-benzoic acid ethyl ester as a white solid. This was used as such in the following reaction.

Workup

  1. temperatureat reflux overnight
  2. customto form
  3. customPrecipitation
  4. customwas completed at 0° C.
  5. filtrationthe solid was filtered
  6. washwashing with ethanol/water 2:1
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-9a5bd98db385417c8a8a9d3b2e6552a5
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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