Nitric Acid → 2-Fluoro-4-hydroxy-5-nitrobenzonitrile

HRID 2070112Notes

Reaction equation

HRID 2070112 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]>C(O)(=O)C>[F:5][C:6]1[CH:13]=[C:12]([OH:14])[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 594440782-Fluoro-4-hydroxy-5-nitrobenzonitrileYield 30.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Nitric acid (0.326 mL, 7.29 mmol) 70% was added dropwise to a stirred solution of 2-fluoro-4-hydroxybenzonitrile (1 g, 7.29 mmol) in acetic acid (20 mL). The resulting solution was warmed to 40° C. for 24 hr. Solvent removed under reduced pressure to afford a yellow solid. Recrystallisation from EtOH (˜15 mL) afforded 2-fluoro-4-hydroxy-5-nitrobenzonitrile (401 mg, 2.202 mmol, 30.2% yield) as a yellow solid.

Workup

  1. customSolvent removed under reduced pressure
  2. customto afford a yellow solid
  3. customRecrystallisation from EtOH (˜15 mL)

Sources & evidence

ORD record
ord-f23297d831684f74abba4a7bb0854fd2
Source dataset
uspto-grants-2012_10
Patent number
US08299257B2

Reaction notes

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