N-bromobutanimide → 4'-(Bromomethyl)-2-cyanobiphenyl

HRID 1416404Notes

Reaction equation

HRID 1416404 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]#[N:15])=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]#[N:15])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1455122-Cyano-4'-methylbiphenyl

Product 1

HCID 15019124'-(Bromomethyl)-2-cyanobiphenylYield 44.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 110 ml of carbon tetrachloride, were added 10.5 g of 4'-methyl-2-cyanobiphenyl, 9.79 g of N-bromosuccinimide and 120 mg of 2,2'-azodiisobutylonitrile, followed by heating under reflux for 2 hours. After hot filtration of the insoluble matter, the filtrate was allowed to cool to room temperature. Crystals so precipitated were collected by filtration, whereby 6.6 g of the title compound was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. filtrationAfter hot filtration of the insoluble matter
  4. customCrystals so precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e840f4a67c284c1d99a8e44a3b6d155b
Source dataset
uspto-grants-1999_06
Patent number
US05912353

Reaction notes

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