Dichloromethane → 1-Bromo-3-(bromomethyl)-5-chlorobenzene

HRID 1432055Notes

Reaction equation

HRID 1432055 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([Cl: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:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH2:9][Br:17])[CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 107746383-Bromo-5-chlorotoluene

Product 1

HCID 223242641-Bromo-3-(bromomethyl)-5-chlorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

Step G2. The mixture of 3-bromo-5-chlorotoluene (9 g, 43.8 mmol), NBS (8.19 g, 46 mmol), and AIBN (200 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-bromo-3-(bromomethyl)-5-chlorobenzene (3) was obtained as a brown residue and used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-766d79b01e7841468bd652aa7394399a
Source dataset
uspto-grants-2009_11
Patent number
US07612069B2

Reaction notes

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