Benzenamine, 2-chloro-5-(trifluoromethyl)- → 4-Bromo-2-chloro-5-(trifluoromethyl)aniline

HRID 1411358Notes

Reaction equation

HRID 1411358 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[CH:11]=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:14][C:15]=1[Cl:16]>CN(C=O)C>[NH2:9][C:10]1[C:15]([Cl:16])=[CH:14][C:13]([Br:1])=[C:12]([C:17]([F:20])([F:18])[F:19])[CH:11]=1

Participants

4

Reactant 2

HCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-HCID 67184N-bromobutanimide

Product 1

HCID 140993984-Bromo-2-chloro-5-(trifluoromethyl)anilineYield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (1.0 g, 5.6 mmol) dissolved in DMF (3 mL) was slowly added to a mixture of 3-amino-4-chlorobenzotrifluoride (1 g, 5 mmol) dissolved in DMF (2 mL) and the reaction mixture was stirred at RT for 20 min, concentrated, and extracted with ethyl acetate/water. The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography (eluted with 100% hexanes) to produce the title intermediate as a reddish colored oil (970 mg, 70% yield). (m/z): [M+H]+ calcd for C7H4BrClF3N, 273.92, 275.92 found 276.2.

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate/water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography (eluted with 100% hexanes)

Sources & evidence

ORD record
ord-f53e2e4b53104b3cab89e47343c2877a
Source dataset
uspto-grants-2014_12
Patent number
US08921372B2

Reaction notes

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