4-Fluorobenzoic Acid → 4-Fluoro-3-nitrobenzoic acid

HRID 1715109Notes

Reaction equation

HRID 1715109 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[N+:11]([O-])([O-:13])=[O:12].[K+]>OS(O)(=O)=O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 99734-Fluorobenzoic AcidHCID 24434Potassium Nitrate

Product 1

HCID 679874-Fluoro-3-nitrobenzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a cold solution of 4-fluorobenzoic acid (50.0 g, 0.36 mol, 1.0 equiv) in concentrated H2SO4 (180 ml) was added portionwise potassium nitrate (39.7 g, 0.39 mol, 1.1 equiv). The reaction mixture was stirred overnight at rt and then poured on crushed ice (800 g) with constant stirring. The resulting mixture was kept overnight at rt, filtered and washed thoroughly with water, and finally dried by making an azeotrope with toluene to yield 59.5 g (90%) of the title compound as a light yellow solid. 1H NMR (400 MHz, DMSO): δ7.69-7.74 (m, 1H), 8.29-8.32 (m, 1H), 8.56 (d, J=7.2 Hz, 1H), 13.75 (br s, 1H).

Workup

  1. additionpoured
  2. waitThe resulting mixture was kept overnight at rt
  3. filtrationfiltered
  4. washwashed thoroughly with water
  5. customfinally dried

Sources & evidence

ORD record
ord-04351b780412424fa587818265a739f1
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

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