Sulfuric Acid → 5-Fluoro-2-nitrobenzonitrile

HRID 618678

Reaction equation

HRID 618678 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[N+:10]([O-])([O-:12])=[O:11].[K+].S(=O)(=O)(O)O>C(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:4]([CH:3]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 678803-Fluorobenzonitrile

Product 1

HCID 37564675-Fluoro-2-nitrobenzonitrileYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Fluorobenzonitrile (25 g) was added dropwise to a stirred mixture of potassium nitrate (21.1 g) and concentrated sulphuric acid (150 ml) which had been cooled in a mixture of salt and ice. The mixture was stirred at ambient temperature for 45 minutes. The mixture was poured onto ice (800 ml) and the precipitate was isolated. The solid so obtained was dissolved in methylene chloride, dried (MgSO4) and the solution was evaporated to give 5-fluoro-2-nitrobenzonitrile (19 g).

Workup

  1. temperaturehad been cooled in a mixture of salt and ice
  2. additionThe mixture was poured onto ice (800 ml)
  3. customthe precipitate was isolated
  4. customThe solid so obtained
  5. dry with materialdried (MgSO4)
  6. customthe solution was evaporated

Sources & evidence

ORD record
ord-cca974b0536343ce985ecaee00ed0664
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Linked notes

Loading…