Azobisisobutyronitrile → 4-(Bromomethyl)-2-methoxybenzonitrile

HRID 2184242Notes

Reaction equation

HRID 2184242 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClCCCl>[Br:12][CH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 124953732-Methoxy-4-methylbenzonitrile

Product 1

HCID 219850074-(Bromomethyl)-2-methoxybenzonitrileYield 35.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4.6 g (31.3 mmol) of 4-methyl-2-methoxybenzonitrile were brominated with 34.7 mmol of N-bromosuccinimide in the presence of catalytic amounts of azobisisobutyronitrile in 60 ml of 1,2-dichloroethane under reflux. 2.5 g of the product were obtained.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-f2c55738ca0045f9a91f7f60d454fdd5
Source dataset
uspto-grants-2005_05
Patent number
US06900319B2

Reaction notes

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