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

HRID 880663

Reaction equation

HRID 880663 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-e86951ee787845a19050816024630467
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Linked notes

Loading…