Water → 4-(Bromomethyl)-3-chlorobenzonitrile

HRID 1922009Notes

Reaction equation

HRID 1922009 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-90db89c82f834c198876efc4f1c3fec4
Source dataset
uspto-grants-2012_05
Patent number
US08173805B2

Reaction notes

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