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

HRID 1757383Notes

Reaction equation

HRID 1757383 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(Cl)(Cl)(Cl)Cl.CCCCCC.C(OOC(=O)C1C=CC=CC=1)(=O)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

6

Reactant 2

HCID 153613,5-DibromotolueneHCID 67184N-bromobutanimide

Product 1

HCID 1434273,5-Dibromobenzyl bromideYield 44%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 8058HexaneSolvent

Procedure

3,5-dibromotoluene (78.92 g, 0.316 mole) was dissolved in 1.27 L of carbon tetrachloride; to this solution was added N-bromosuccinimide (61.65 g, 0.346 mole) at room temperature. A portion of dibenzoyl peroxide (0.6 g, 0.008 equivalents) was added and the solution heated to reflux temperaturefor 2.5 hours. The reaction mixture was cooled to room temperature, filtered and the solvent removed in vacuo to yield a solid. The solid was dissolved in 200 mL of warm hexane, filtered and cooled to room temperature. Crystallizations ensued; the crystals were filtered off and washed with cold hexane and air dried to give 45.15 g (44%) of 3,5-dibromobenzyl bromide. 1H-NMR(CDCl); δ 7.6 (1H), 7.47(2H), 4.36 (2H).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux temperaturefor 2.5 hours
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customto yield a solid
  6. filtrationfiltered
  7. temperaturecooled to room temperature
  8. customCrystallizations
  9. filtrationthe crystals were filtered off
  10. washwashed with cold hexane and air
  11. customdried

Sources & evidence

ORD record
ord-ed606e265a2b4c1792f1ab39a36e39ca
Source dataset
uspto-grants-1995_08
Patent number
US05446039

Reaction notes

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