Benzoyl Peroxide → [(2-Methoxy-6-methylphenyl)methyl](triphenyl)phosphanium bromide

HRID 1667301Notes

Reaction equation

HRID 1667301 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:27][C:28]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:29]=1[O:35][CH3:36].[C:37]1([P:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)(Cl)(Cl)Cl.C1C=CC=CC=1>[Br-:1].[CH3:36][O:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([CH3:34])[C:28]=1[CH2:27][P+:43]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

7

Reactant 4

HCID 7187Benzoyl PeroxideHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 762692,3-Dimethylanisole

Product 1

HCID 71323067[(2-Methoxy-6-methylphenyl)methyl](triphenyl)phosphanium bromideYield 61.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

After 4.34 g of N-bromosuccinimide and 0.54 g of benzoyl peroxide were added to a solution of 3.03 g of 2,3-dimethylanisole in 70 ml of carbon tetrachloride, the mixture was heated under reflux for 30 minutes. After cooling, insoluble solid in the reaction mixture were filtered off and the filtrate was concentrated under reduced pressure to give an oil. The obtained oil was dissolved in 50 ml of benzene, and 5.82 g of triphenylphosphine was added to the solution. The mixture was heated under reflux for 11 hours. After cooling, the precipitated crystals were collected by filtration and recrystallized from methylene chloride-benzene to give 6.51 g of (2-methoxy-6-methylbenzyl)(triphenyl)phosphonium bromide as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. filtrationinsoluble solid in the reaction mixture were filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give an oil
  7. temperatureThe mixture was heated
  8. temperatureunder reflux for 11 hours
  9. temperatureAfter cooling
  10. filtrationthe precipitated crystals were collected by filtration
  11. customrecrystallized from methylene chloride-benzene

Sources & evidence

ORD record
ord-0e509fef62494341913bfd5e189bd3d0
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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