Chlorosuccinimide → 4-Bromo-2-chloro-5-(trifluoromethoxy)benzenamine

HRID 2176448Notes

Reaction equation

HRID 2176448 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:9][C:10]([F:13])([F:12])[F:11].[Cl:14]N1C(=O)CCC1=O>C(#N)C>[Br:1][C:2]1[C:3]([O:9][C:10]([F:12])([F:11])[F:13])=[CH:4][C:5]([NH2:8])=[C:6]([Cl:14])[CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 141291984-Bromo-3-(trifluoromethoxy)aniline

Product 1

HCID 674959584-Bromo-2-chloro-5-(trifluoromethoxy)benzenamineYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

To a mixture of 4-bromo-3-trifluoromethoxy-phenylamine (2.0 g, 7.8 mmol) in ACN (60 mL) was slowly added a solution of N-chlorosuccinimide (1.0 g, 7.8 mmol) in ACN (40 mL). The reaction mixture was heated at 60° C. overnight and extracted with ethyl acetate/water. The organic layer was dried over sodium sulfate and purified by flash chromatography (40 g column, 100% hexanes to 10% EtOAc:hexanes) to produce the desired product as an orange-ish-colored oil (1.4 g, 64% yield).

Workup

  1. extractionextracted with ethyl acetate/water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. custompurified by flash chromatography (40 g column, 100% hexanes to 10% EtOAc:hexanes)

Sources & evidence

ORD record
ord-ab44db31c03644eebb2fac6f59a27a5d
Source dataset
uspto-grants-2015_06
Patent number
US09066944B2

Reaction notes

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