Benzoyl Peroxide → 3-Acetoxy-4-tert-butylbenzyl bromide

HRID 744784Notes

Reaction equation

HRID 744784 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:27]([O:30][C:31]1[CH:32]=[C:33]([CH3:41])[CH:34]=[CH:35][C:36]=1[C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:29])[CH3:28]>C(Cl)(Cl)(Cl)Cl>[C:27]([O:30][C:31]1[CH:32]=[C:33]([CH:34]=[CH:35][C:36]=1[C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:41][Br:1])(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 214587813-Acetoxy-4-tert-butyltoluene

Product 1

HCID 214587573-Acetoxy-4-tert-butylbenzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

16.4 g of N-bromosuccinimide, 1 g of α,α'-azoisobutyronitrile and 1 g of dibenzoyl peroxide are added in succession to a solution, stirred at 70° C., of 19 g of 3-acetoxy-4-tert-butyltoluene in 900 ml of CCl4. The reaction mixture is stirred under reflux for 31/2 hours under UV irradiation and is filtered, and the filtrate is concentrated by evaporation. The title compound is obtained from the residue by means of FC (900 g of silica gel, hexane/ethyl acetate=95:5): Rf (hexane/ethyl acetate=95:5)=0.40.

Workup

  1. temperatureunder reflux for 31/2 hours
  2. customunder UV irradiation
  3. filtrationis filtered
  4. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-2db2b567619e40d38ebf8b8b82da218d
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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