Potassium Nitrate → 4-Fluoro-2-methyl-5-nitrobenzonitrile

HRID 2064193Notes

Reaction equation

HRID 2064193 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[N+:11]([O-])([O-:13])=[O:12].[K+]>S(=O)(=O)(O)O>[F:1][C:2]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 38260554-Fluoro-2-methylbenzonitrile

Product 1

HCID 573458874-Fluoro-2-methyl-5-nitrobenzonitrileYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Fluoro-2-methylbenzonitrile (10 mmol, 1.35 g) was dissolved in concentrated sulphuric acid (10 mL) under argon then treated with potassium nitrate (10 mmol, 1.01 g, 1 eq) at 0° C. portionwise to keep the temperature around 0° C. The mixture was allowed to stir for 2 h while warming up to room temperature. The mixture was then poured onto ice and extracted twice with ether. The organics were combined, dried and concentrated under reduced pressure to give the title compound as a solid (9.4 mmol, 1.7 g, 94% yield).

Workup

  1. customthe temperature around 0° C
  2. additionThe mixture was then poured onto ice
  3. extractionextracted twice with ether
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ff9a5edf52d462eacc409f31e38642e
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

Loading…