N-bromobutanimide → 1-Bromo-2-(bromomethyl)-3,5-dichlorobenzene

HRID 2352555Notes

Reaction equation

HRID 2352555 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[CH2:10][Br:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 102636612-Bromo-4,6-dichlorotoluene

Product 1

HCID 104260681-Bromo-2-(bromomethyl)-3,5-dichlorobenzeneYield 45.8%

Reagents, catalysts & solvents 1

HCID 7187Benzoyl PeroxideCatalyst

Procedure

Stir slowly, an intimate mixture of 220 g of 2-bromo-4,6-dichlorotoluene, 167 g of N-bromosuccinimide and 1 g of benzoyl peroxide in a flask (equipped with a condenser and stirrer) immersed in an 145° C. oil bath. After 10-20 min a vigorous eruption occurs and the mixture liquifies. Remove the oil bath and stir for an additional 5 min. Add 1.5 L of CCl4 slowly through the condenser. Cool the mixture and suction filter the resulting reaction mixture. Wash the filtrate with 5% aqueous sodium thiosulfate, dry over anhydrous K2CO3, filter and evaporate to a residue. Fractionally distill the residue to give 134 g of 2-bromo-4,6-dichlorobenzyl bromide, bp 94°-97° C. (0.2 tor).

Workup

  1. custom(equipped with a condenser and stirrer)
  2. customimmersed in an 145° C.
  3. customRemove the oil bath
  4. stirringstir for an additional 5 min
  5. additionAdd 1.5 L of CCl4 slowly through the condenser
  6. temperatureCool the mixture and suction
  7. filtrationfilter
  8. customthe resulting reaction mixture
  9. washWash the filtrate with 5% aqueous sodium thiosulfate
  10. dry with materialdry over anhydrous K2CO3
  11. filtrationfilter
  12. customevaporate to a residue
  13. distillationFractionally distill the residue

Sources & evidence

ORD record
ord-e9947ccb2d6f4ac48eb13b85f8c080c6
Source dataset
uspto-grants-1989_10
Patent number
US04877801

Reaction notes

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