N-bromobutanimide → 4-Bromo-2-chloro-6-(trifluoromethyl)aniline

HRID 2067796Notes

Reaction equation

HRID 2067796 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[C:11]=1[NH2:12]>C(#N)C.C(O)(=O)C>[Br:1][C:15]1[CH:14]=[C:13]([C:17]([F:19])([F:18])[F:20])[C:11]([NH2:12])=[C:10]([Cl:9])[CH:16]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27563842-Chloro-6-(trifluoromethyl)aniline

Product 1

HCID 162179374-Bromo-2-chloro-6-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (910 mg, 5.1 mmol) was added to a solution of 2-chloro-6-(trifluoromethyl)aniline (1.0 g, 5.1 mmol) in acetonitrile (10 mL) and acetic acid (3 mL) at room temperature. The mixture was stirred at reflux to 18 h. The reaction mixture was then filtered through Celite and concentrated to give the title compound which was used in the next step without further purification.

Workup

  1. temperatureat reflux to 18 h
  2. filtrationThe reaction mixture was then filtered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2bea2ac6acf449788c6e80715390d6d6
Source dataset
uspto-grants-2012_10
Patent number
US08293911B2

Reaction notes

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