Water → 4-(Bromomethyl)-3-chlorobenzonitrile

HRID 1510938Notes

Reaction equation

HRID 1510938 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[C:5]#[N:6].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 888943-Chloro-p-toluonitrile

Product 1

HCID 130420934-(Bromomethyl)-3-chlorobenzonitrileYield 98.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-chloro-4-methylbenzonitrile (7.5 g, 50 mmol, 1.0 equiv), N-bromosuccinimide (9.14 g, 52 mmol, 1.1 equiv), and azobisisobutyronitrile (AIBN, 0.82 g, 5 mmol, 0.1 equiv) in carbon tetrachloride was heated to reflux temperature for 25 h. Water (50 mL) was added, and the product was extracted with CH2Cl2. The organic layers were washed with water, dried with MgSO4, and evaporated to provide 11.3 g of the title compound. This material was used in the next step without purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature for 25 h
  3. extractionthe product was extracted with CH2Cl2
  4. washThe organic layers were washed with water
  5. dry with materialdried with MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-4da80bac64454843810f6f324a1a30c0
Source dataset
uspto-grants-2012_07
Patent number
US08212032B2

Reaction notes

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