Azobisisobutyronitrile → 2-(Bromomethyl)-6-chlorobenzonitrile

HRID 1752245Notes

Reaction equation

HRID 1752245 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:11][CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 230532-Chloro-6-methylbenzonitrileHCID 67184N-bromobutanimide

Product 1

HCID 667339472-(Bromomethyl)-6-chlorobenzonitrileYield 46.7%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-6-methylbenzonitrile (2.0 g, 13 mmol) and N-bromosuccinimide (2.6 g, 15 mmol) in carbon tetrachloride (20 mL) was added azobisisobutyronitrile (0.20 g, 1.2 mmol). The mixture was refluxed for 3 h and then cooled, diluted with dichloromethane and washed with water and brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resultant oil was purified via flash column chromatography (ethyl acetate:hexane, 0:100 to 30:70) to yield white solid product (1.4 g, 46%). 1H NMR (400 MHz, CDCl3) δ 7.43-7.59 (m, 3H), 4.64 (s, 2H).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. temperaturecooled
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant oil was purified via flash column chromatography (ethyl acetate:hexane, 0:100 to 30:70)

Sources & evidence

ORD record
ord-15bbc06972cc442d96d857f173004298
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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