Water → 4'-(Bromomethyl)-2-cyanobiphenyl

HRID 567395Notes

Reaction equation

HRID 567395 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])=[CH:4][CH:3]=1.C1C(=O)N([Br:23])C(=O)C1.N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N.O>ClCCl>[Br:23][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)HCID 1455122-Cyano-4'-methylbiphenyl

Product 1

HCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
47.5 °C

Procedure

A mixture of 2-(4-methylphenyl)benzonitrile [MPB] 23 g, NBS 22 g and 2,2′-azobis(2,4-dimethylvaleronitrile) 47 mg was suspended in dichloromethane 44 ml and the mixture was stirred at 45-50° C. for about 5 hours. To the reaction mixture was added water 46 ml and the organic layer was separated. This operation was conducted three times. The organic layer was concentrated and acetonitrile 50 ml was added to the concentrate. The solution was again concentrated and acetonitrile 50 ml was added to the concentrate to give acetonitrile solution of 2-(4-bromomethylphenyl)benzonitrile [BMB] (116 g; Yield based on the theoretical amount of (2-(4-bromomethylphenyl)benzonitrile: 84%).

Workup

  1. customthe organic layer was separated
  2. concentrationThe organic layer was concentrated
  3. additionacetonitrile 50 ml was added to the concentrate
  4. concentrationThe solution was again concentrated
  5. additionacetonitrile 50 ml was added to the
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-5d95aa9553a643719258ae75233917cc
Source dataset
uspto-grants-2001_01
Patent number
US06177587B1

Reaction notes

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