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

HRID 2067777Notes

Reaction equation

HRID 2067777 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-4facba097ab9464489f28b7bcbcead6b
Source dataset
uspto-grants-2012_10
Patent number
US08293911B2

Reaction notes

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