Nitric Acid → 4-Fluoro-3-nitrobenzoic acid

HRID 2292250Notes

Reaction equation

HRID 2292250 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.[N+:16]([O-])([OH:18])=[O:17]>>[N+:16]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:7]=1[F:6])[C:11]([OH:13])=[O:12])([O-:18])=[O:17]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 99734-Fluorobenzoic Acid

Product 1

HCID 679874-Fluoro-3-nitrobenzoic acid

Conditions

Temperature
0 °C

Procedure

150 ml of nitric acid with a density of 1.42 were added at 0° C. to 300 ml of concentrated sulfuric acid and 50 g of p-fluoro-benzoic acid were added thereto at 0° C. over 30 minutes. The mixture was stirred at 0° C. for one hour and the temperature was allowed to rise to 20° C. The mixture was stirred at 20° C. for 16 hours and was poured over ice. The mixture was vacuum filtered and the product was washed and dried to obtain 47.6 g of 3-nitro-4-fluoro-benzoic acid melting at 123°-124° C. The said product was reacted as in Step B of Example 1 to obtain 0-(2-nitro-4-carboxy-phenyl)-hydroxylamine melting at 215° C.

Workup

  1. additionwere added
  2. customto rise to 20° C
  3. stirringThe mixture was stirred at 20° C. for 16 hours
  4. additionwas poured over ice
  5. filtrationfiltered
  6. washthe product was washed
  7. customdried

Sources & evidence

ORD record
ord-d0d55e425922426cb4e57f4e49129916
Source dataset
uspto-grants-1989_01
Patent number
US04801717

Reaction notes

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