Aniline → HCID 20554540, compound

HRID 1659596Notes

Reaction equation

HRID 1659596 reaction equation
C1(N)C=CC=CC=1.[N+:8]([C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([N+:21]([O-:23])=[O:22])[C:12]=1[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])[CH:26]=1)([O-:10])=[O:9].[Cl:39]Cl>ClCCl>[N+:21]([C:13]1[CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[C:12]=1[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:37])([F:38])[C:33]([F:34])([F:35])[F:36])[C:26]=1[Cl:39])([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 6115AnilineHCID 24526ChlorineHCID 20554533HCID 20554533, compound

Product 1

HCID 20554540HCID 20554540, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

When desired, the above described halogenation reaction can be carried out utilizing less than one molar quantity of halogenating agent, thereby effecting monohalogenation instead of dihalogenation. The monohalogenated product can be further halogenated if desired with the same or a different halogenating agent. For instance a benzenamine such as N-(2,6-dinitro-4-trifluoromethylphenyl)-3-(1,1,2,2,2-pentafluoroethoxy)benzenamine can be reacted with about a 0.5 molar amount of chlorine in dichloromethane at about 25° C. to give N-(2,6-dinitro-4-trifluoromethylphenyl)-2-chloro-3-(1,1,2,2,2-pentafluoroethoxy)benzenamine. The latter compound can be further halogenated, for instance by reaction with about a 0.5 to 1.0 molar amount of bromine in dichloromethane, to provide the corresponding dihalogenated derivative, for example N-(2,6-dinitro-4-trifluoromethylphenyl)-2-chloro-4-bromo-5-(1,1,2,2,2-pentafluoroethoxy)benzenamine.

Workup

  1. customhalogenation reaction

Sources & evidence

ORD record
ord-9c7d6df808cd4dab824a4eb89854a1d9
Source dataset
uspto-grants-1981_12
Patent number
US04304791

Reaction notes

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