Acetic Acid → 4-Bromo-2-chloro-6-(trifluoromethyl)aniline

HRID 880655

Reaction equation

HRID 880655 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(O)(=O)C>C(#N)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 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 27563842-Chloro-6-(trifluoromethyl)aniline

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-bromo succinimide (910 mg, 5.1 mmol) was added to a solution of 2-chloro-6-(trifluoromethyl)aniline (1.0 g, 5.1 mmol) and acetic acid (3 mL) in acetonitrile (10 mL) at room temperature. The mixture was heated at reflux, with stirring, for 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. temperatureThe mixture was heated
  2. temperatureat reflux
  3. filtrationThe reaction mixture was then filtered through Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-62cbed9771e744a78af50d42da7422b1
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Linked notes

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