2,6-Dichlorotoluene → 1-Bromo-2,4-dichloro-3-methylbenzene

HRID 1013801Notes

Reaction equation

HRID 1013801 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH3:9].[Br:10]Br>C(Cl)(Cl)(Cl)Cl.[Fe].II>[Br:10][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:9])[C:4]=1[Cl:8]

Participants

6

Reactant 2

HCID 83682,6-DichlorotolueneHCID 24408Bromine

Product 1

HCID 148011751-Bromo-2,4-dichloro-3-methylbenzeneYield 102.2%

Reagents, catalysts & solvents 3

HCID 807IodineCatalystHCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Treat a mixture of 2,6-dichlorotoluene (50.0 g, 0.31 mol), iodine (0.10 g, 0.39 mmol), and 325 mesh iron powder (0.70 g, 12.5 mmol) in CCl4 (60 mL) dropwise with bromine (52.8 g, 0.33 mol) over 20 minutes and is stir for 3 hours at room temperature. Pour the mixture into ice water and extract with 1,2-dichloroethane. Wash the organic layer with saturated sodium bisulfite and dry using Na2SO4. Remove the solvent in vacuo to afford 76.01 g (100%) 1-bromo-2,4-dichloro-3-methyl-benzene.

Workup

  1. additionTreat
  2. extractionextract with 1,2-dichloroethane
  3. washWash the organic layer with saturated sodium bisulfite
  4. customdry
  5. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-4958faac45c44685a907fac990163d18
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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