N-bromobutanimide → 4-Bromo-4-(4-chlorophenyl)-3,3-dimethylbutan-2-one

HRID 2119061Notes

Reaction equation

HRID 2119061 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:14])([CH3:13])[C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([Br:15])[C:9]([CH3:14])([CH3:13])[C:10](=[O:12])[CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 128706324-(4-Chlorophenyl)-3,3-dimethylbutan-2-one

Product 1

HCID 132771714-Bromo-4-(4-chlorophenyl)-3,3-dimethylbutan-2-oneYield 82%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

50 g (0.237 mol) of 1-(4-chlorophenyl)-2,2-dimethyl-3-butanone are dissolved in 500 ml of tetrachloromethane, and 44.5 g (0.25 mol) of N-bromosuccinimide and 0.5 g of azobisisobutyronitrile are added. The reaction mixture is heated to boiling under reflux until solid material no longer sinks to the bottom on switching off the stirrer. After cooling down, the succinimide is filtered off with suction, the solvent is distilled off from the filtrate under waterpump vacuum and the residue is distilled under high vacuum. 56.3 g (82% of theory) of 1-(4-chlorophenyl)-1-bromo-2,2-dimethyl-3-butanone of boiling point 112°-118° C./0.2 mbar are obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux until solid material
  3. temperatureAfter cooling down
  4. filtrationthe succinimide is filtered off with suction
  5. distillationthe solvent is distilled off from the filtrate under waterpump vacuum
  6. distillationthe residue is distilled under high vacuum

Sources & evidence

ORD record
ord-41bd04e92b6d421d88bf0ff0df3a671d
Source dataset
uspto-grants-1987_07
Patent number
US04681952

Reaction notes

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