3-Bromotoluene → 3-Bromobenzyl bromide

HRID 556121Notes

Reaction equation

HRID 556121 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>ClC(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Br:9])[CH:3]=1

Participants

5

Reactant 2

HCID 115603-BromotolueneHCID 67184N-bromobutanimide

Product 1

HCID 699793-Bromobenzyl bromideYield 84.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-bromotoluene (42.8 g, 0.25 mol), N-bromosuccinimide (48.9 g, 0.275 mol) and benzoyl peroxide (0.75 g) in tetrachloromethane (500 mL) was stirred and heated to reflux for 3 h. The mixture was left to stand overnight at laboratory temperature, the solid was filtered off, washed with tetrachloromethane and the filtrates were evaporated. The residue was distilled in vacuo to yield 52.7 g (62.5%) of 1-bromo-3-bromomethylbenzene, b.p. 135-140° C./1.6 kPa.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. waitThe mixture was left
  4. filtrationthe solid was filtered off
  5. washwashed with tetrachloromethane
  6. customthe filtrates were evaporated
  7. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-62b162f4579a429b9888f07bda64b2f5
Source dataset
uspto-grants-2011_11
Patent number
US08053598B2

Reaction notes

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