Ethanol → Ethyl 2-fluoro-4-nitrobenzoate

HRID 2241165Notes

Reaction equation

HRID 2241165 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, 5.0 mmol) in ethanol (10.0 ml) was treated with concentrated sulfuric acid (0.30 ml) and stirred at reflux overnight. On cooling to room temperature and then to 0° C. a crystalline precipitate formed. This was filtered washing with ethanol/water 2:1, and dried under vacuum, yielding 2-fluoro-4-nitro-benzoic acid ethyl ester (0.75 g, 65%) as an off-white crystalline solid.

Workup

  1. temperatureat reflux overnight
  2. customto 0° C. a crystalline precipitate formed
  3. filtrationThis was filtered
  4. washwashing with ethanol/water 2:1
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d0ed9dbf331149978818e6fd778ec9bf
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

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