Nitric Acid → 5-Fluoro-2-hydroxy-3-nitrobenzoic acid

HRID 654042Notes

Reaction equation

HRID 654042 reaction equation
[F:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>C(#N)C>[F:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 676585-Fluorosalicylic acid

Product 1

HCID 152546965-Fluoro-2-hydroxy-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

6.24 g (40 mmol) of 5-fluoro-salicylic acid is dissolved in 62.4 ml of acetonitrile with warming, the solution is cooled to 0° C. and, with this temperature being maintained a solution of 2.96 ml (44 mmol) of 65% HNO3 in 14.8 ml of acetonitrile is instilled. The reaction mixture is stirred for 24 hours at 0° C., then filtered over 7.5 g of silica gel 60 and evaporated to dryness 6.1 g =75.8% of the theoretical yield is obtained of the crude product, which is used in the next reaction without purification.

Workup

  1. temperaturewith warming
  2. filtrationfiltered over 7.5 g of silica gel 60
  3. customevaporated to dryness 6.1 g =75.8% of the
  4. customtheoretical yield

Sources & evidence

ORD record
ord-cd1dbf9c844040039dcc7af49aaf899e
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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