Nitric Acid → 5-Fluoro-2-nitrobenzoic acid

HRID 1767490Notes

Reaction equation

HRID 1767490 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[N+:11]([O-])([OH:13])=[O:12]>OS(O)(=O)=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:4]([CH:3]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 99683-Fluorobenzoic Acid

Product 1

HCID 27374205-Fluoro-2-nitrobenzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

3-Fluorobenzoic acid (1 g, 7.13 mmol) was dissolved in concentrated H2SO4 (2 ml) by warming slightly above room temperature. The solution was cooled to 0° C. Fuming nitric acid (539 mg, 8.56 mmol) was added slowly to the solution while keeping the temperature below 0° C. The solution was stirred at 0° C. for 3 h. The solution was poured into ice water, the solid formed were filtered, washed by cold water, and dried to yield 1.2 g (92%) of white solids. M.P. 122° C. 1H NMR (DMSO-d6): 7.60 (dt, J=2.9, 8.5 Hz, 1H), 7.71 (dd, J=2.9, 8.6 Hz, 1H), 8.13 (dd, J=4.8, 8.8 Hz, 1H). EIMS m/z 186 (M+1).

Workup

  1. temperatureby warming slightly above room temperature
  2. customthe temperature below 0° C
  3. customthe solid formed
  4. filtrationwere filtered
  5. washwashed by cold water
  6. customdried

Sources & evidence

ORD record
ord-90a4f5d73b8345138d967c67a7dfc77a
Source dataset
uspto-grants-2007_06
Patent number
US07235546B2

Reaction notes

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