N-bromobutanimide → HCID 57656172, compound

HRID 911585Notes

Reaction equation

HRID 911585 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[O:5].C1C(=O)N([Br:22])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:1][C:2]([CH3:14])([CH3:13])[CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][Br:22])=[CH:10][CH:11]=1)=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178606563,3-Dimethyl-1-(4-methylphenyl)butan-1-one

Product 1

HCID 57656172HCID 57656172, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Heat a mixture of 3,3,4′-trimethylbutyrophenone (2 g, 10.52 mmol), NBS (2.061 g, 11.57 mmol), and AIBN (43 mg, 0.263 mmol) in carbon tetrachloride (60 mL) for 14 h at reflux. Cool the reaction, mixture to ambient temperature and wash sequentially with water, 1M aqueous HCl, 5% aqueous NaHCO3 and brine. Concentrate the organic layer in vacuo to provide the desired intermediate as oil (2.54 g, 90%) that was used without any further purification.

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. temperatureCool
  4. customthe reaction, mixture to ambient temperature
  5. washwash sequentially with water, 1M aqueous HCl, 5% aqueous NaHCO3 and brine
  6. concentrationConcentrate the organic layer in vacuo

Sources & evidence

ORD record
ord-948103f00c4f43f49d3eb7f27b121fd4
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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