Benzoyl Peroxide → 3,4-Dimethoxybenzyl bromide

HRID 2258540Notes

Reaction equation

HRID 2258540 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 681263,4-Dimethoxytoluene

Product 1

HCID 109004583,4-Dimethoxybenzyl bromideYield 50%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 15.2 g of 3,4-dimethoxytoluene, 17.8 g of N-bromosuccinimide and 0.3 g of dibenzoyl peroxide in 100 ml of CCl4 is heated at reflux for hours, under illumination from a UV lamp. The precipitate is drained off and the filtrate is evaporated under vacuum. The residue is taken up in ether, washed with water, dried over Na2SO4 and evaporated under vacuum. An oil is obtained which contains a mixture of 50% of the expected product and 50% of the starting material, which mixture is used without further purification in the subsequent synthesis.

Workup

  1. temperatureis heated
  2. temperatureat reflux for hours, under illumination from a UV lamp
  3. customthe filtrate is evaporated under vacuum
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum
  7. customAn oil is obtained which

Sources & evidence

ORD record
ord-caddcf50549148c197047aadcfe813fe
Source dataset
uspto-grants-1997_08
Patent number
US05661169

Reaction notes

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