Azobisisobutyronitrile → 4-(Bromomethyl)-3-methoxybenzonitrile

HRID 2184233Notes

Reaction equation

HRID 2184233 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:6]#[N:7].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:31])C(=O)C1.CCCCCCC>ClCCCl>[Br:31][CH2:11][C:10]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 8900HeptaneHCID 67184N-bromobutanimideHCID 147529943-Methoxy-4-methylbenzonitrile

Product 1

HCID 147529954-(Bromomethyl)-3-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
82 °C

Procedure

14.7 g (0.1 mol) of 3-methoxy-4-methylbenzonitrile were dissolved in 210 ml of 1,2-dichloroethane, bromination was carried out at 82° C. in the presence of catalytic amounts of AIBN with 19.1 g (0.11 mol) of NBS in portions over the course of 1 h and, after the addition was complete, the mixture was stirred at 82° C. for a further 30 min. Addition of n-heptane was followed by removal of precipitated succinimide, and the solvent was stripped off. The product contained, besides small amounts of precursor, also traces of the corresponding benzal bromide. 1H-NMR (DMSO-d6; δ in ppm): 7.60 (dd, 1H); 7.50 (d, 1H); 7.40 (dd, 1H); 4.68 (s, 2H); 3.96 (s, 3H)

Workup

  1. additionafter the addition
  2. customwas followed by removal of precipitated succinimide

Sources & evidence

ORD record
ord-e217318264f3410fa81c8f5b61354f24
Source dataset
uspto-grants-2005_05
Patent number
US06900319B2

Reaction notes

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