Chlorosuccinimide → 2-Chloro-4-(1-bromo-1,1,2,3,3,3-hexafluoro-2-propyl)aniline

HRID 1824583Notes

Reaction equation

HRID 1824583 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]([F:25])([F:24])[C:11]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)([F:16])[C:12]([F:15])([F:14])[F:13]>C(#N)C>[Cl:1][C:22]1[CH:23]=[C:17]([C:11]([F:16])([C:12]([F:15])([F:14])[F:13])[C:10]([Br:9])([F:24])[F:25])[CH:18]=[CH:19][C:20]=1[NH2:21]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 230649694-(1-Bromo-1,1,2,3,3,3-hexafluoro-2-propyl)aniline

Product 1

HCID 230649712-Chloro-4-(1-bromo-1,1,2,3,3,3-hexafluoro-2-propyl)aniline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

18.24 g (0.14 mol) of N-chlorosuccinimide were added at 60° C. to a mixture of 40.0 g (0.12 mol) of 4-(1-bromo-1,1,2,3,3,3-hexafluoro-2-propyl)aniline from Example 6 and 125 ml of acetonitrile, and the resulting mixture was heated to reflux for 3 hours. Subsequently, the solvent was for the most part distilled off, the residue was washed with 100 ml of 1N NaOH solution, the organic phase was dried over sodium sulphate and finally the remaining solvent was removed under reduced pressure.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 hours
  3. distillationdistilled off
  4. washthe residue was washed with 100 ml of 1N NaOH solution
  5. dry with materialthe organic phase was dried over sodium sulphate
  6. customfinally the remaining solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-087a73ebddc249a882c41cb366dcbd60
Source dataset
uspto-grants-2006_05
Patent number
US07041852B2

Reaction notes

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