4-Bromotoluene → 4-Bromobenzyl bromide

HRID 1739502Notes

Reaction equation

HRID 1739502 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78054-BromotolueneHCID 67184N-bromobutanimide

Product 1

HCID 685274-Bromobenzyl bromideYield 59.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a suspension of 4-bromotoluene (60 g) and N-bromosuccinimide (69 g) in carbon tetrachloride (300 ml) was added 2,2'-azobis(isobutylonitrile) (0.1 g). The resulting mixture was heated under reflux for 2 hours. After the reaction mixture was cooled, succinimide so precipitated was removed by filtration, and the filtrate was washed with saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous magnesium sulfate, followed by removal through distillation. The oily substance so obtained was crystallized from n-hexane, whereby 52 g of the title compound was obtained.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter the reaction mixture was cooled
  4. customsuccinimide so precipitated
  5. customwas removed by filtration
  6. washthe filtrate was washed with saturated aqueous sodium hydrogencarbonate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customfollowed by removal through distillation
  9. customThe oily substance so obtained
  10. customwas crystallized from n-hexane

Sources & evidence

ORD record
ord-2cee7facc5384698845343dd65382108
Source dataset
uspto-grants-1999_10
Patent number
US05965738

Reaction notes

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