N-bromobutanimide → 4-Bromo-3-chloro-5-(trifluoromethyl)aniline

HRID 1048864Notes

Reaction equation

HRID 1048864 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[Br:13]N1C(=O)CCC1=O>CS(C)=O>[Br:13][C:8]1[C:7]([C:9]([F:10])([F:11])[F:12])=[CH:6][C:4]([NH2:5])=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 30179333-Chloro-5-(trifluoromethyl)aniline

Product 1

HCID 299348454-Bromo-3-chloro-5-(trifluoromethyl)anilineYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 3-chloro-5-(trifluoromethyl)aniline (3.25 g, 16.6 mmol, Eq: 1.00) in dimethylsulfoxide (43.4 ml) was added N-bromosuccinimide (3.11 g, 17.4 mmol, Eq: 1.05) in 5 portions over 2.5 hr (622 mg each 30 min). 2 h after the last addition, the reaction mixture was partitioned between 10% aqueous sodium sulfite and ethyl acetate. The organic layer was washed with aqueous sat. sodium carbonate, water (3 times) and brine then adsorbed unto silica (6 g) and purified on silica gel (column 120 g, Hexane/ethyl acetate 90:10 to 65:35) to give 4.36 g (96%) of a yellow solid.

Workup

  1. addition2 h after the last addition
  2. customthe reaction mixture was partitioned between 10% aqueous sodium sulfite and ethyl acetate
  3. washThe organic layer was washed with aqueous sat. sodium carbonate, water (3 times) and brine
  4. custompurified on silica gel (column 120 g, Hexane/ethyl acetate 90:10 to 65:35)

Sources & evidence

ORD record
ord-6361e42c79404b32949c8ddd4bc52540
Source dataset
uspto-grants-2016_07
Patent number
US09382218B2

Reaction notes

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