Nitric Acid → 2-Fluoro-5-nitrobenzonitrile

HRID 1489596Notes

Reaction equation

HRID 1489596 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9]>S(=O)(=O)(O)O>[F:5][C:6]1[CH:13]=[CH:12][C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 678552-Fluorobenzonitrile

Product 1

HCID 5194172-Fluoro-5-nitrobenzonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 70% nitric acid and concentrated sulfuric acid (1:1, 30 mL) is added dropwise over 30 min to a solution of 2-fluorobenzonitrile (12.11 g, 0.10 mol) in concentrated sulfuric acid (50 mL), stirred under N2 at 0° C. After a further 3h at 0° C. the yellow solution is poured onto ice (400 g), and the solid is collected by Buchner filtration, rinsed with water (4×50 mL), and dried in vacuo to give 2-fluoro-5-nitrobenzonitrile (15.43 g, 93%) as a pale yellow crystalline solid. 1H NMR (CDCl3) δ8.56 (1H, dd, J=2.8, 5.5 Hz), 8.51 (1H, ddd, J=2.8, 4.4, 9.1 Hz), 7.44 (1H, dd, J=7.8, 9.0 Hz).

Workup

  1. filtrationthe solid is collected by Buchner filtration
  2. washrinsed with water (4×50 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-fb8ee092515c4bee988ab9076e817767
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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