Benzoyl Peroxide → HCID 54300424, compound

HRID 483901Notes

Reaction equation

HRID 483901 reaction equation
[CH3:1][C@@H:2]([CH2:14][CH3:15])[CH2:3][O:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1.[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][C@@H:2]([CH2:14][CH3:15])[CH2:3][O:4][C:5]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][Br:16])=[CH:10][CH:11]=1)=[O:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18652760HCID 18652760, compound

Product 1

HCID 54300424HCID 54300424, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

20.63 g (0.1 mole) of the 4-methylbenzoic acid[(S)-2-methylbutyl]ester obtained in Step A-1, 17.80 g (0.1 mole) of N-bromosuccinimide, and 1.32 g (0.005 moles) of benzoyl peroxide were dissolved in 120 ml of dry carbon tetrachloride and allowed to react under reflux for three hours. On completion of the reaction, the reaction mixture was filtered while hot to remove the succinimide, which is a by-product of the reaction, and 27.70 g of a crude form of the objective 4-((S)-2-methyl butoxycarbonyl)benzylbromide was obtained from the filtrate by evaporating off the carbon tetrachloride.

Workup

  1. customto react
  2. temperatureunder reflux for three hours
  3. customOn completion of the reaction
  4. filtrationthe reaction mixture was filtered while hot
  5. customto remove the succinimide, which
  6. customa by-product of the reaction, and 27.70 g of a crude form of the objective 4-((S)-2-methyl butoxycarbonyl)benzylbromide
  7. customwas obtained from the filtrate
  8. customby evaporating off the carbon tetrachloride

Sources & evidence

ORD record
ord-7a5bc267c7db480e8c07b2a8ee71040c
Source dataset
uspto-grants-1993_07
Patent number
US05227512

Reaction notes

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