Sulfuric Acid → 2-Chloro-4-fluoro-5-nitrotoluene

HRID 231406Notes

Reaction equation

HRID 231406 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[CH3:14].[N+:15]([O-])([O-:17])=[O:16].[K+]>C(Cl)CCl>[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][C:8]=1[CH3:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 967472-Chloro-4-fluorotoluene2×

Product 1

HCID 101039792-Chloro-4-fluoro-5-nitrotolueneYield 91.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Concentrated sulfuric acid (250 ml) was added to a stirred solution of 2-chloro-4-fluorotoluene (50.0 g, 0.346 mole) in ethylene dichloride (250 ml) at 0° C. Potassium nitrate (35.0 g, 0.346 mole) was then added slowly, maintaining the temperature below 10° C. The reaction was monitored by gas chromatography. Upon the disappearance of 2-chloro-4-fluorotoluene, the reaction mixture was poured into ice and extracted with methylene chloride. The dried organic layer was concentrated under reduced pressure to yield 60.0 g of 2-chloro-4-fluoro-5-nitrotoluene. This reaction was repeated several times.

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. extractionextracted with methylene chloride
  3. concentrationThe dried organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c6d9be9bc3244770900092ffc5658d22
Source dataset
uspto-grants-1989_07
Patent number
US04846875

Reaction notes

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