Potassium Nitrate → 2-Chloro-4-fluoro-5-nitrotoluene

HRID 388544Notes

Reaction equation

HRID 388544 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([O-:12])=[O:11].[K+]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 24434Potassium Nitrate2×HCID 967472-Chloro-4-fluorotoluene

Product 1

HCID 101039792-Chloro-4-fluoro-5-nitrotoluene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 100 g (0.7 mol) of 2-chloro-4-fluorotoluene in 250 ml of concentrated H2SO4 is added portion-wise 85 g (0.875 mol) of KNO3 at 0° C. (addition of the whole amount of KNO3 is finished in about 1 hour). The reddish mixture is slowly warmed-up at room temperature overnight and quenched over crushed ice and extracted with EtOAc. The organic layers are combined, dried over MgSO4 and concentrated. The crude oil is then purified over a large silica plug (eluent: 97/3 hexanes/EtOAc) to afford 2-chloro-4-fluoro-5-nitrotoluene as a pale yellow oil that solidifies upon standing. 1H NMR (CDCl3, 400 Mz): 7.97 (d, J=8.0 Hz, 1H), 7.32 (d, J=10.4 Hz, 1H), 2.43 (s, 3H).

Workup

  1. customquenched
  2. customover crushed ice
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude oil is then purified over a large silica plug (eluent: 97/3 hexanes/EtOAc)

Sources & evidence

ORD record
ord-ffaa7644869a4c08812157ae660f6306
Source dataset
uspto-grants-2013_02
Patent number
US08377921B2

Reaction notes

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