Nitric Acid → 2-(2,6-Difluoro-3-nitrophenyl)acetonitrile

HRID 243241Notes

Reaction equation

HRID 243241 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]#[N:11].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[F:1][C:2]1[C:7]([N+:12]([O-:14])=[O:13])=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]#[N:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 69559(2,6-Difluorophenyl)acetonitrile

Product 1

HCID 665453902-(2,6-Difluoro-3-nitrophenyl)acetonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of (2,6-difluorophenyl)acetonitrile (5 g, 32.7 mmol) in conc. Sulphuric acid (15 mL) at −78° C. was added dropwise a solution of nitric acid (65%, 2.25 mL, 32.7 mmol) in conc. sulphuric acid (5 mL). On completion of addition the reaction mixture was poured onto ice and the precipitate that formed collected by filtration, washed with water and dried in vacuo to give the title product as a white solid (6.4 g, 100%). 1H NMR 400 MHz δ (CDCl3): 8.24-8.16 (1H, m), 7.17 (1H, ddd, J=9.6, 7.8, 1.9 Hz), 3.84 (2H, t, J=1.2 Hz).

Workup

  1. additionOn completion of addition the reaction mixture
  2. additionwas poured onto ice
  3. customthe precipitate that formed
  4. filtrationcollected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-553d695e9ce347edac99071ea44be865
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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