3,5-Dibromotoluene → 3,5-Dibromobenzyl bromide

HRID 1356849Notes

Reaction equation

HRID 1356849 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.[Br:10]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Br:8])[CH:7]=1)[CH2:9][Br:10]

Participants

5

Reactant 2

HCID 153613,5-DibromotolueneHCID 67184N-bromobutanimide

Product 1

HCID 1434273,5-Dibromobenzyl bromideYield 48.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

3,5-Dibromotoluene (27.0 g; 108.0 mmol), N-bromosuccinimide (19.2 g; 108.0 mmol), and benzoyl peroxide (0.32 g) were added to benzene (200 ml), and the mixture was refluxed for 2.5 hours. The mixture was brought to room temperature, and the solvent was evaporated under reduced pressure. The residue was taken up in n-hexane (200 ml), and the mixture was left to stand overnight at room temperature. Crystals that precipitated were filtered off, and the filtrate was concentrated under reduced pressure, to thereby yield 17.2 g of the target compound (yield: 48.3%).

Workup

  1. temperaturethe mixture was refluxed for 2.5 hours
  2. customwas brought to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. waitthe mixture was left
  5. customCrystals that precipitated
  6. filtrationwere filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2d83f1b3541c4f0697bc3cda43e9175d
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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