Chlorine → HCID 19819658, compound

HRID 1031128Notes

Reaction equation

HRID 1031128 reaction equation
[Cl:1]Cl.[N+:3]([C:6]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:7]=1[NH2:8])([O-:5])=[O:4]>C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:9]1[CH:10]=[C:11]([O:13][C:14]([F:15])([F:16])[F:17])[CH:12]=[C:6]([N+:3]([O-:5])=[O:4])[C:7]=1[NH2:8]

Participants

5

Reactant 2

HCID 24526Chlorine2×HCID 27757722-Nitro-4-(trifluoromethoxy)aniline

Product 1

HCID 19819658HCID 19819658, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Chlorine gas was passed through a solution of 2-nitro-4-trifluoromethoxy-aniline (14.5g) in carbon tetrachloride (175ml). The stirred mixture became solid, and more carbon tetrachloride (50ml) was added. Chlorine gas was passed through the reaction mixture until thin layer chromatography on silica gel, using petroleum ether (boiling range 60-80° C.) containing ethyl acetate (30% by volume) as eluent, demonstrated the absence of starting material. Evaporation of the solvent under reduced pressure gave a dark orange solid, which on trituration with petroleum ether (boiling range 60-80° C.) gave 2-chloro-4-trifluoromethoxy-6-nitroaniline as an orange solid.

Workup

  1. additionwas added
  2. customEvaporation of the solvent under reduced pressure
  3. customgave a dark orange solid, which on trituration with petroleum ether (boiling range 60-80° C.)

Sources & evidence

ORD record
ord-4014f9e9892d43bcbe7b5eed5544c89f
Source dataset
uspto-grants-1992_04
Patent number
US05109004

Reaction notes

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