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

HRID 2067788Notes

Reaction equation

HRID 2067788 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-bromosuccinimide (910 mg, 5.1 mmol) was added at room temperature to a solution of 2-chloro-6-(trifluoromethyl)aniline (1.0 g, 5.1 mmol) and acetic acid (3 mL) in acetonitrile (10 mL). 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 and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5609fc1644074b4a805bf641ee01957e
Source dataset
uspto-grants-2012_10
Patent number
US08293911B2

Reaction notes

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