3,5-Dimethylchlorobenzene → 1-(Bromomethyl)-3-chloro-5-methylbenzene

HRID 1760021Notes

Reaction equation

HRID 1760021 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH3:9])[CH:3]=1)[CH2:8][Br:17]

Participants

5

Reactant 2

HCID 328873,5-DimethylchlorobenzeneHCID 67184N-bromobutanimide

Product 1

HCID 123755491-(Bromomethyl)-3-chloro-5-methylbenzeneYield 81.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 5-chloro-m-xylene (14.06 g; 0.1 mol), NBS (17.8 g; 0.1 mol) and AIBN (1.1 g; 6.7 mmol) in CCl4 was refluxed for two hours. The resultant mixture was cooled, and the solid material formed was removed by filtration. Concentration yielded the sub-title compound (17.9 g; 80%).

Workup

  1. customthe solid material formed
  2. customwas removed by filtration
  3. concentrationConcentration

Sources & evidence

ORD record
ord-dcaf00f291a4451595d49f43f0f3613b
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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