N-bromobutanimide → 2-Bromo-5-methoxybenzyl bromide

HRID 1937768Notes

Reaction equation

HRID 1937768 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O>ClC(Cl)C.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][Br:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1179151-Bromo-4-methoxy-2-methylbenzene

Product 1

HCID 35259512-Bromo-5-methoxybenzyl bromideYield 64%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-bromo-5-methoxytoluene (50 g, 0.25 mol) in dichloroethane (375 ml), N-bromosuccinimide (48.8 g, 0.275 mol) and AIBN (1.36 g) were added and the reaction was refluxed for 4 h. The cooled solution was filtered and the solvent was evaporated to give a weight of 44.8 g crude 1-Bromo-2-bromomethyl-4-methoxy-benzene (64% yield). This compound was used in next step without further purification.

Workup

  1. temperaturethe reaction was refluxed for 4 h
  2. filtrationThe cooled solution was filtered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f980ff73bd2d4899a6d0a3f6e72613d1
Source dataset
uspto-grants-2002_05
Patent number
US06395911B1

Reaction notes

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