Nitric Acid → 1,2-Dichloro-3-nitro-5-(trifluoromethyl)benzene

HRID 461863Notes

Reaction equation

HRID 461863 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[Cl:8].S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:10])[F:11])[CH:5]=[C:6]([N+:18]([O-:20])=[O:19])[C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 94813,4-Dichlorobenzotrifluoride

Product 1

HCID 27740301,2-Dichloro-3-nitro-5-(trifluoromethyl)benzeneYield 18.1%

Conditions

Temperature
95 °C

Procedure

3,4-Dichloro-α,α,α-trifluorotoluene (862 g. 4.0 mols) is added to a stirred mixture of concentrated sulfuric acid (4400 g.) and nitric acid (3400 g.) at 35° C. The mixture is stirred 70 minutes at 95° C. and allowed to separate. The oil layer is washed once with water and twice with 5% sodium carbonate solution, dried, and fractionally distilled to give 3,4dichloro-5-nitro-α,α,α-trifluorotoluene (188 g. 18%) b.p. 115°-118° C./15 mm, 88% pure.

Workup

  1. customto separate
  2. washThe oil layer is washed once with water and twice with 5% sodium carbonate solution
  3. customdried
  4. distillationfractionally distilled

Sources & evidence

ORD record
ord-f228cd7c9c884df89b254e8a1f08f174
Source dataset
uspto-grants-1977_12
Patent number
US04063929

Reaction notes

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