2,4-Dichlorotoluene → 2-Bromo-4,6-dichlorotoluene

HRID 2352554Notes

Reaction equation

HRID 2352554 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][CH:3]=1.[Br:10]Br>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:10][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[C:5]=1[CH3:9]

Participants

5

Reactant 2

HCID 72542,4-DichlorotolueneHCID 24408Bromine3×

Product 1

HCID 102636612-Bromo-4,6-dichlorotolueneYield 213.1%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 32 g of 4,6-dichlorotoluene and 0.3 g of anhydrous FeCl3, add, with stirring, 10 g of bromine in 1 g portions while maintaining a temperature of 20°-25° C. Add thereto a solution of 22 g of bromine in 100 mL of CCl4 slowly while maintaining a temperature of 20°-25° C. After the addition of bromine is complete, stir the mixture so formed for 15 min, and dilute the reaction mixture with 200 mL of CH2Cl2, and wash the organic solution with 5% aqueous sodium thiosulfate. Dry the organic layer over anhydrous K2CO3, filter, and evaporate to a residue. Recrystallize the residue from CH3CN to give 32 g of 2-bromo-4,6-dichlorotoluene, mp 84°-5° C.

Workup

  1. additionadd
  2. additionAdd
  3. stirringstir the mixture
  4. customso formed for 15 min
  5. washwash the organic solution with 5% aqueous sodium thiosulfate
  6. dry with materialDry the organic layer over anhydrous K2CO3
  7. filtrationfilter
  8. customevaporate to a residue
  9. customRecrystallize the residue from CH3CN

Sources & evidence

ORD record
ord-3a1ad3b4b1314eada886b5ac5c73aa55
Source dataset
uspto-grants-1989_10
Patent number
US04877801

Reaction notes

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