Ethanol → Ethyl 4-fluoro-3-nitrobenzoate

HRID 2292254Notes

Reaction equation

HRID 2292254 reaction equation
S(=O)(=O)(O)O.[N+:6]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[F:18])[C:12]([OH:14])=[O:13])([O-:8])=[O:7].O.[CH2:20](O)[CH3:21]>>[N+:6]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[F:18])[C:12]([O:14][CH2:20][CH3:21])=[O:13])([O-:8])=[O:7]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric Acid2×HCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Conditions

Temperature
20 °C

Procedure

2 ml of concentrated sulfuric acid were added to a solution of 10 g of 3-nitro-4-fluoro-benzoic acid in 50 ml of ethanol and the mixture was refluxed for three hours. 8 ml of concentrated sulfuric acid were added to the mixture which was refluxed for 16 hours and was cooled to 20° C. The mixture was poured into water with stirring and was filtered. The solid product was washed and dried to obtain 10.5 g of ethyl 3-nitro-4-fluoro-benzoate melting at 50° C. The said product was reacted as in Example 1 to obtain 0-(4-ethoxycarbonyl-2-nitro-phenyl)-hydroxylamine melting at 102° C.

Workup

  1. temperaturethe mixture was refluxed for three hours
  2. temperaturewas refluxed for 16 hours
  3. filtrationwas filtered
  4. washThe solid product was washed
  5. customdried

Sources & evidence

ORD record
ord-640599fb3df64e3bb891facde9534960
Source dataset
uspto-grants-1989_01
Patent number
US04801717

Reaction notes

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