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

HRID 880670Notes

Reaction equation

HRID 880670 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-46e88b1d8ed54073b4c51ceea8ccfa76
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

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