3-Bromotoluene → 3-Bromobenzyl bromide

HRID 1356782Notes

Reaction equation

HRID 1356782 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[Br:9]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][Br:9]

Participants

5

Reactant 2

HCID 115603-BromotolueneHCID 67184N-bromobutanimide

Product 1

HCID 699793-Bromobenzyl bromideYield 67.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

m-bromotoluene (25.33 g; 148.1 mmol), N-bromosuccinimide (26.36 g; 148.1 mmol), and benzoyl peroxide (0.3 g) were added to carbon tetrachloride (200 ml), and the mixture was heated under reflux for 3 hours. The white crystals that precipitated were filtered off, and the filtrate was concentrated under reduced pressure. The residue was taken up in n-hexane (200 ml), and the mixture was left to stand for 15 hours at room temperature. The white crystals that precipitated were filtered off, and the filtrate was concentrated, to thereby yield a yellow oily compound (25.1 g). The compound was analyzed by 1H-NMR and found to be a mixture of the target compound, the starting compound, and a dibromo compound (4.34:1.03:1.00). The yield based on the result of 1H-NMR analysis was 67.9%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customThe white crystals that precipitated
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. waitthe mixture was left
  7. customThe white crystals that precipitated
  8. filtrationwere filtered off
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-60228af5e3284ff99368737acdbd57bc
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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