Sulfuric Acid → 2,4-Difluoro-5-nitrobenzonitrile

HRID 1092221Notes

Reaction equation

HRID 1092221 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].OS(O)(=O)=O.[F:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>>[F:11][C:12]1[CH:19]=[C:18]([F:20])[C:17]([N+:1]([O-:4])=[O:2])=[CH:16][C:13]=1[C:14]#[N:15]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 775452,4-Difluorobenzonitrile

Product 1

HCID 118197152,4-Difluoro-5-nitrobenzonitrileYield 95%

Procedure

Potassium nitrate (16.4 g, 147.4 mmol) was added to concentrated H2SO4 (85 ml, 1582 mmol) at 0° C., followed by slow addition of 2,4-difluorobenzonitrile (11.0 g, 79.1 mmol). The suspension was stirred at this temperature for an additional 4 hrs and quenched ice/water (800 ml). The resulting solid was collected by filtration and dried to give the title compound (13.8 g, 95%) as a white solid. NMR (400 MHz, CDCl3) 8.48 (m, 1H), 7.24 (m, 1H).

Workup

  1. customquenched ice/water (800 ml)
  2. filtrationThe resulting solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-a9beb9f8543642be8a4a13350551dd9b
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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