N-bromobutanimide → HCID 59828861, compound

HRID 911707Notes

Reaction equation

HRID 911707 reaction equation
[CH3:1][CH:2]([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:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:1][CH:2]([CH3:13])[CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][Br:21])=[CH:10][CH:11]=1)=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 125064723-Methyl-1-(4-methylphenyl)butan-1-one

Product 1

HCID 59828861HCID 59828861, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Heat a mixture of 3,4′-dimethylbutyrophenone (3 g, 17.02 mmol), NBS (3.787 g, 16.18 mmol), and AIBN (70 mg, 0.425 mmol) in carbon tetrachloride (80 mL) for 14 h at reflux. Cool to ambient temperature and filter the mixture. Concentrate the filtrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (9:1) to provide the title compound as oil (2.802 g, 65%). GC-MS m/z: 255 (M+).

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. filtrationfilter the mixture
  4. concentrationConcentrate the filtrate in vacuo
  5. customPurify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-01512d9e18ca42dca2e163eee359bf3f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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