Nitric Acid → 5-Fluoro-2-nitrophenylacetic acid

HRID 971425Notes

Reaction equation

HRID 971425 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:17]([O-:19])=[O:18])=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:3]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 676173-Fluorophenylacetic acid

Product 1

HCID 103978545-Fluoro-2-nitrophenylacetic acid

Procedure

To a mixture of 23.2 g. of 3-fluorophenylacetic acid and 100 ml. of conc. sulfuric acid is added dropwise 6.5 ml. of conc. nitric acid while maintaining the temperature below 40° C. The mixture is stirred at ambient temperature for 24 hours and then poured onto one kilogram of ice. The resulting precipitate is recovered by filtering, washed with water and dried in vacuo to obtain crude 5-fluoro-2-nitrophenylacetic acid, m.p. 137°-142° C.

Workup

  1. additionTo a mixture of 23.2 g
  2. customThe resulting precipitate is recovered
  3. filtrationby filtering
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f65beccf1c5b4335bc87eff3e3a5e6b4
Source dataset
uspto-grants-1979_07
Patent number
US04160032

Reaction notes

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