2,5 Dibromotoluene → 1,4-Dibromo-2-(bromomethyl)benzene

HRID 742475

Reaction equation

HRID 742475 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH3:9].C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOCC1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH2:9][Br:17]

Participants

5

Reactant 2

HCID 120062,5 DibromotolueneHCID 67184N-bromobutanimide

Product 1

HCID 53260381,4-Dibromo-2-(bromomethyl)benzeneYield 55.7%

Reagents, catalysts & solvents 2

HCID 11229634Benzyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 75 g (0.3 mol) of 2,5-dibromotoluene in 1 L of carbon tetrachloride was added 58.73 g (0.33 mol) of NBS and 50 mg of benzyl peroxide, and the resulting mixture was refluxed with stirring for 24 h. The mixture was cooled, and concentrated in vacuo. The residue was crystallized from hot methanol and washed with hexane to afford 54.5 g (55.7%) of 2.5-dibromobenzyl bromide as a solid.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customThe residue was crystallized from hot methanol
  5. washwashed with hexane

Sources & evidence

ORD record
ord-d1e95f67272f45da9c565ac04bac9e84
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Linked notes

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