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

HRID 1656559Notes

Reaction equation

HRID 1656559 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 temperature for 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(CDCl3); δ 7.6 (1H), 7.47 (2H), 4.36 (2H).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux temperature for 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-e9424b948b9945bbb74333dd4241f2fe
Source dataset
uspto-grants-1993_10
Patent number
US05254683

Reaction notes

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