Benzoyl Peroxide → 1-Phenyl-3-(o-anisyloxy)propylbromide

HRID 1706498Notes

Reaction equation

HRID 1706498 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]1([CH2:15][CH2:16][CH2:17][O:18][CH2:19][C:20]2[C:21]([O:26][CH3:27])=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:9]1([CH:15]([Br:1])[CH2:16][CH2:17][O:18][CH2:19][C:20]2[C:21]([O:26][CH3:27])=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 152084201-Methoxy-2-[(3-phenylpropoxy)methyl]benzene

Product 1

HCID 203360451-Phenyl-3-(o-anisyloxy)propylbromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Using a similar procedure to that above, a reaction mixture was prepared containing 48 g. of N-bromosuccinimide, 65 g. of 1-phenyl-3-(o-anisyloxy)propane and 300 ml. of carbon tetrachloride. 500 mg. of benzoyl peroxide were added and the resulting mixture heated at reflux for about 2 hours at which point thin-layer chromatography indicated that no starting material remained in the reaction mixture. The reaction mixture was cooled, the succinimide separated by filtration and the solvent removed from the filtrate by evaporation in vacuo. A residual oil weighing about 88 g. comprising 1-phenyl-3-(o-anisyloxy)propylbromide formed in the above reaction was obtained.

Workup

  1. customwas prepared
  2. additioncontaining 48 g
  3. temperaturethe resulting mixture heated
  4. temperatureat reflux for about 2 hours at which point thin-layer chromatography
  5. temperatureThe reaction mixture was cooled
  6. customthe succinimide separated by filtration
  7. customthe solvent removed from the filtrate by evaporation in vacuo

Sources & evidence

ORD record
ord-4ac83b515d464eeabfe186be56067547
Source dataset
uspto-grants-1980_06
Patent number
US04207343

Reaction notes

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