Benzoyl Peroxide → 1-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-

HRID 1700006Notes

Reaction equation

HRID 1700006 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(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[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 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 987444-Chloro-4'-isopropylbutyrophenone

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Dissolve 4-chloro-1-(4-isopropyl-phenyl)-butan-1-one (2.10 g, 9.35 mmol) in carbontetrachloride (30 mL), add N-bromosuccinimide (1.75 g, 9.83 mmol) and benzoylperoxide (3 mg) and stir at reflux for 1 hour. Cool the reaction mixture, filter, wash with water and brine. Dry (MgSO4), filter and evaporate the solvent in vacuo to give the title compound as an amber oil.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureCool the reaction mixture
  3. filtrationfilter
  4. washwash with water and brine
  5. dry with materialDry (MgSO4)
  6. filtrationfilter
  7. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-95fb6776d2404f0499b8229987ad4a21
Source dataset
uspto-grants-2002_02
Patent number
US06348597B2

Reaction notes

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