Benzoyl Peroxide → (3-bromoprop-1-en-2-yl)benzene

HRID 1664783Notes

Reaction equation

HRID 1664783 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH3:29])=[CH2:28]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:28][C:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[CH2:29]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 7407Alpha-MethylstyreneHCID 67184N-bromobutanimide2×

Product 1

HCID 234998(3-bromoprop-1-en-2-yl)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (52.0 g, 292 mmol) and benzoylperoxide (2.0 g, 8.0 mmol) were added to a solution of isopropenylbenzene (82.0 g, 694 mmol) in carbon tetrachloride (200 mL). The reaction mixture was heated to reflux. After 18 h, additional N-bromosuccinimide (30.0 g, 168 mmol) was added. After 18 h, the mixture was allowed to cool to ambient temperature and the solid in the mixture was filtered off. The filtrate was concentrated and purified by vacuum distillation (95-120° C., 10 torr). The isolated mixture was purified by silica gel chromatography (100% hexanes) to give the title compound.

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. waitAfter 18 h
  3. filtrationthe solid in the mixture was filtered off
  4. concentrationThe filtrate was concentrated
  5. distillationpurified by vacuum distillation (95-120° C., 10 torr)
  6. customThe isolated mixture was purified by silica gel chromatography (100% hexanes)

Sources & evidence

ORD record
ord-b510f49c7624455da190c6064c8d0134
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

Loading…