Azobisisobutyronitrile → 4-(Bromomethyl)-3-methoxybenzonitrile

HRID 1584091Notes

Reaction equation

HRID 1584091 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].C1C(=O)N([Br:19])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N.CCCCCCC>ClCCCl>[Br:19][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, brominated with 19.1 g (0.11 mol) of NBS in portions over the course of 1 h in the presence of catalytic amounts of azobisisobutyronitrile at 82° C. and, after the addition was complete, stirred at 82° C. for a further 30 min. After addition of n-heptane, precipitated succinimide was removed, and the solvent was stripped off. The yield was 18.5 [lacuna] (82%). 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. customprecipitated succinimide
  3. customwas removed

Sources & evidence

ORD record
ord-a70b1cee28474c20a530e68e6ca676cd
Source dataset
uspto-grants-1999_08
Patent number
US05932567

Reaction notes

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