Benzoyl Peroxide → 4-(3-Tert-butoxy carbonyl phenyl)benzyl bromide

HRID 735845Notes

Reaction equation

HRID 735845 reaction equation
[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:28])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6]([C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][Br:28])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)=[O:20])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18398672Tert-butyl-3-(4-tolyl)benzoate

Product 1

HCID 183986744-(3-Tert-butoxy carbonyl phenyl)benzyl bromideYield 85.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of tert-Butyl-3-(4-tolyl)benzoate (60 g, 0.22 mol) in CCl4 (800 mL) were added NBS (47.8 g, 0.268 mol) and benzoylperoxide (10 g) and the reaction mixture was refluxed overnight. Cooled to RT and filtered. The filtrate was concentrated to give 4-(3-tert-butoxy carbonyl phenyl)benzyl bromide (65 g, 84%).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e118c6b6916249c2947361c569b40e32
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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