N-bromobutanimide → 1-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-

HRID 1018072Notes

Reaction equation

HRID 1018072 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)=[O:6].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:16][C:13]([C:10]1[CH:9]=[CH:8][C:7]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])=[CH:12][CH:11]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 987444-Chloro-4'-isopropylbutyrophenone

Product 1

HCID 100635791-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-Yield 100.9%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

Dissolve 4-chloro-1-(4-isopropyl-phenyl)-butan-1-one (5.00 g, 22.2 mmol) and N-bromosuccinimide (4.1 g, 23.0 mmol) in carbon tetrachloride (25 mL) and add AIBN radical initiator (300 mg). Stir and maintain under a nitrogen atmosphere at 80-90° C. or optionally irradiate with a sunlamp until a vigorous exotherm occurs at which point momentarily remove until reflux subsides and then reapply the heat. Reflux for 30 minutes and add another potion of N-bromosuccinimide (100 mg) while maintaining reflux and reflux an additional 15 minutes. Cool to room temperature and precipitate the succinimide from the solution by allowing to stand overnight. Filter and wash the succinimide (2.25 g) with carbon tetrachloride (20 mL). Combine the filtrates and evaporate the solvent in vacuo to give the title compound as a yellow oil (6.80 g, 100%).

Workup

  1. customoptionally irradiate with a sunlamp until a vigorous exotherm
  2. custommomentarily remove
  3. temperatureuntil reflux subsides
  4. temperatureReflux for 30 minutes
  5. additionadd another potion of N-bromosuccinimide (100 mg)
  6. temperaturewhile maintaining
  7. temperaturereflux
  8. temperaturereflux an additional 15 minutes
  9. temperatureCool to room temperature
  10. customprecipitate the succinimide from the solution
  11. filtrationFilter
  12. washwash the succinimide (2.25 g) with carbon tetrachloride (20 mL)
  13. customCombine the filtrates and evaporate the solvent in vacuo

Sources & evidence

ORD record
ord-995e3d6976de4b818da0a55f60a693e4
Source dataset
uspto-grants-2002_11
Patent number
US06479663B2

Reaction notes

Loading…