Sulfuric Acid → 4-Fluoro-3-nitrobenzonitrile

HRID 2379131Notes

Reaction equation

HRID 2379131 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1.[N+:15]([O-])([O-:17])=[O:16].[K+]>>[F:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 145174-FluorobenzonitrileHCID 24434Potassium Nitrate

Product 1

HCID 27746544-Fluoro-3-nitrobenzonitrile

Conditions

Temperature
0 °C

Procedure

The largest amount of silica gel that still allowed the resulting slurry to be stirred magnetically at 0° C., was added to conc. sulfuric acid (125 ml). To this mixture 4-fluorobenzonitrile (12.5 g, 103 mmol) was added followed by potassium nitrate (10.4 g, 103 mmol). The reaction mixture was stirred at 0° C. for 20 minutes. The sulfuric acid was removed from the product by passing the mixture through a short column of silica gel and the product was washed out with methylene chloride. The solvent was evaporated to leave the product as a crystalline solid. Yield 6.0 g, mp 86°-88° C.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 20 minutes
  2. customThe sulfuric acid was removed from the product
  3. washthe product was washed out with methylene chloride
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d295273e7f2b4c9e98fd641905e476ad
Source dataset
uspto-grants-1994_11
Patent number
US05360809

Reaction notes

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