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

HRID 2269222Notes

Reaction equation

HRID 2269222 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[Br:10][CH2:3][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 7407Alpha-MethylstyreneHCID 67184N-bromobutanimide

Product 1

HCID 234998(3-bromoprop-1-en-2-yl)benzeneYield 51.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Benzene (120 ml), was mixed with 9.00 g (76.2 mmol), of α-methylstyrene, 14.2 g (80.0 mmol), of N-bromosuccinimide, and 300 mg of benzoyl peroxide and the mixture was refluxed for 24 hours. After the solvent was distilled off under reduced pressure, carbon tetrachloride was added and the resulting crystals were filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (n-hexane 100%), to obtain the target compound. The yield, % yield and NMR spectrum were as follows. Yield: 7.72 g, % yield: 51.5%.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. distillationAfter the solvent was distilled off under reduced pressure, carbon tetrachloride
  3. additionwas added
  4. filtrationthe resulting crystals were filtered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (n-hexane 100%)
  7. customto obtain the target compound

Sources & evidence

ORD record
ord-d96042b0e100448e8e8f383712c7d801
Source dataset
uspto-grants-2001_12
Patent number
US06329399B1

Reaction notes

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