Potassium Nitrate → 2,4-Difluoro-5-nitrobenzonitrile

HRID 1858009Notes

Reaction equation

HRID 1858009 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[F:6][C:7]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:8]=1[C:9]#[N:10]>S(=O)(=O)(O)O>[F:6][C:7]1[CH:14]=[C:13]([F:15])[C:12]([N+:1]([O-:4])=[O:2])=[CH:11][C:8]=1[C:9]#[N:10]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 775452,4-Difluorobenzonitrile

Product 1

HCID 118197152,4-Difluoro-5-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of potassium nitrate (73.2 g, 0.718 mmol, 2 eq) and concentrated sulfuric acid (350 mL) was cooled to 0° C. and 2,4-difluorobenzonitrile was added in portions over 10 to 15 minutes. The mixture was stirred for 30 minutes and then poured onto ice to give a precipitate. The precipitate was isolated by filtration, washed with water and lyophilized to provide 2,4-difluoro-5-nitrobenzonitrile (50 g, 0.28 mol) as an off-white solid; PB-CI/MS: 185=(MH+); 1H-NMR (300 Mhz, DMSO-d6): 8.093(t, 1H), 8.982(t, 1H).

Workup

  1. additionpoured onto ice
  2. customto give a precipitate
  3. customThe precipitate was isolated by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-4728ab3a2ef341f290bcd9722539f20d
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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