Benzoyl Peroxide → HCID 67185680, compound

HRID 735862Notes

Reaction equation

HRID 735862 reaction equation
[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[Br:21]N1C(=O)CCC1=O.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:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([CH2:19][Br:21])=[CH:17][CH:18]=2)=[CH:9][CH:8]=1)=[O:20])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67186699HCID 67186699, compound

Product 1

HCID 67185680HCID 67185680, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of tert-butyl-4-(4-tolyl)benzoate (32 g, 0.12 mol) in carbontetrachloride (500 mL) was added N-bromosuccinimide (23.3 g, 0.13 mol) and benzoyl peroxide (4.0 g). The reaction mixture was refluxed for 10 h. After cooling to RT, the reaction mixture was filtered. The filtrate was concentrated and the crude was recrystallised from petEther to give 4-(4-tert-butoxycarbonylphenyl)benzylbromide (26 g, 69%).

Workup

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. filtrationthe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated
  4. customthe crude was recrystallised from petEther

Sources & evidence

ORD record
ord-16e17688f9c04bcdb04c6c1cf927e956
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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