Azobisisobutyronitrile → 4-(Bromomethyl)-2-methoxybenzonitrile

HRID 378326Notes

Reaction equation

HRID 378326 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. 1H-NMR (DMSO-d6, δ in ppm): 7.75 (d, 1H), 7.35 (s, broad, 1H), 7.15 (d, broad, 1H), 4.73 (s, 2H), 3.95 (s, 3H)

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-cb015b0a30b246fa99e426201e5d5552
Source dataset
uspto-grants-2000_02
Patent number
US06030972

Reaction notes

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