Nitric Acid → 3-Fluoro-4-hydroxy-5-nitrobenzonitrile

HRID 1258740Notes

Reaction equation

HRID 1258740 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[OH:14])[C:9]#[N:10]>OS(O)(=O)=O>[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([N+:1]([O-:4])=[O:2])[C:13]=1[OH:14])[C:9]#[N:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27829443-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 679577893-Fluoro-4-hydroxy-5-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

Fuming HNO3 (1.8 mL; 44 mmol) was added dropwise to a solution of 3-fluoro-4-hydroxybenzonitrile (4.0 g; 29 mmol) in conc. H2SO4 (10 mL) at −10° C. The mixture was stirred at −10° C. for 1 h and thereafter slowly poured into ice. The precipitate was filtered off and the filtrate was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was combined with the precipitate and crystallized from EtOAc/PE to give the sub-title compound.

Workup

  1. additionslowly poured into ice
  2. filtrationThe precipitate was filtered off
  3. extractionthe filtrate was extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customcrystallized from EtOAc/PE

Sources & evidence

ORD record
ord-af31975989c84987a67bbf305a6cd574
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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