Dichloromethane → 3,5-Dibromobenzyl bromide

HRID 1432058Notes

Reaction equation

HRID 1432058 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.C1C(=O)N([Br:17])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.ClCCl>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][Br:17])[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6547AzobisisobutyronitrileHCID 153613,5-DibromotolueneHCID 67184N-bromobutanimide

Product 1

HCID 1434273,5-Dibromobenzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

Step H1. A mixture of 3,5-dibromo-toluene (4.25 g, 17 mmol), NBS (3 g, 17 mmol), and AIBN (150 mg) in carbon tetrachloride (50 mL) was heated at 80° C. for 3 hours. The resulting mixture was run through a silicon gel column with dichloromethane as the eluant. The fraction was collected and solvent was removed by rotovap, crude 1,3-dibromo-5-(bromomethyl)benzene was obtained as a white residue.

Workup

  1. customThe fraction was collected
  2. customsolvent was removed by rotovap

Sources & evidence

ORD record
ord-5f6af8584f41428590fe1d19723add88
Source dataset
uspto-grants-2009_11
Patent number
US07612069B2

Reaction notes

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