Water → 4-Bromo-1-(bromomethyl)-2-chlorobenzene

HRID 133186

Reaction equation

HRID 133186 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C1C(=O)N([Br:17])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.O>C(Cl)(Cl)(Cl)Cl>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][Br:17])=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27355544-Bromo-2-chlorotoluene

Product 1

HCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneYield 55.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5.0 g of 2-chloro-4-bromotoluene are dissolved in 120 ml of CCl4. 4.3 g of NBS and 1.6 g of AIBN are added. The mixture is heated at reflux for 15 hours, water is added, the two phases are separated and then extraction is carried out with CH2Cl2. Purification is carried out by chromatography on a silica column eluted with petroleum ether. 3.8 g of liquid are obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 15 hours
  3. customthe two phases are separated
  4. extractionextraction
  5. customPurification
  6. washeluted with petroleum ether

Sources & evidence

ORD record
ord-c412f9599aac43f2abfff64456467fa1
Source dataset
uspto-grants-2008_06
Patent number
US07390818B2

Linked notes

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