N-bromobutanimide → 2-Bromo-6-chlorobenzyl bromide

HRID 128244Notes

Reaction equation

HRID 128244 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][Br:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1235522-Bromo-6-chlorotoluene

Product 1

HCID 27568722-Bromo-6-chlorobenzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-bromo-6-chlorotoluene (20.55 g) and N-bromosuccinimide (19.6 g) were stirred together in carbon tetrachloride (100 ml) under reflux for 22 hours exposure to radiation from an infrared lamp. The resulting solution was cooled in ice, filtered and evaporated to yield the title product which was dissolved in petroleum ether (60-80). Part was recrystallised therefrom as pink needles (8.5 g) and part was recovered by evaporation as a dark orange solid (17.7 g) (total yield 26.2 g. 92%).

Workup

  1. temperatureunder reflux for 22 hours exposure to radiation from an infrared lamp
  2. temperatureThe resulting solution was cooled in ice
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-1beeabfd933d4bed91e4baad702c8eeb
Source dataset
uspto-grants-1981_03
Patent number
US04259349

Reaction notes

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