4'-(Bromomethyl)-2-cyanobiphenyl → 2-Cyano-4'-methylbiphenyl

HRID 443078Notes

Reaction equation

HRID 443078 reaction equation
Br[CH:2](Br)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1.BrCC1C=CC(C2C=CC=CC=2C#N)=CC=1>C1(C)C=CC=CC=1>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 111002274'-(Dibromomethyl)[1,1'-biphenyl]-2-carbonitrile

Product 1

HCID 1455122-Cyano-4'-methylbiphenyl

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After the dropwise addition of the solution prepared by dissolving the mixture of 4'-dibromomethyl-2-cyanobiphenyl and 4'-bromomethyl-2-cyanobiphenyl in toluene was terminated, the mixture was allowed to react up to a point where the above suspension no longer absorbs hydrogen gas. After the reaction was terminated, Raney catalyst and sodium carbonate were filtered off, and the reaction mixture was then concentrated to distill off methanol and toluene. The resulting crude 4'-methyl-2-cyanobiphenyl was purified by distillation, to give 7.4 g of 4'-methyl-2-cyanobiphenyl having an LC purity of 98.2%.

Workup

  1. additionAfter the dropwise addition of the solution
  2. customprepared
  3. dissolutionby dissolving
  4. customwas terminated
  5. customto react up to a point where the above suspension no longer absorbs hydrogen gas
  6. customAfter the reaction was terminated
  7. filtrationRaney catalyst and sodium carbonate were filtered off
  8. concentrationthe reaction mixture was then concentrated
  9. distillationto distill off methanol and toluene
  10. distillationThe resulting crude 4'-methyl-2-cyanobiphenyl was purified by distillation

Sources & evidence

ORD record
ord-aa50b0f8aff3430c92ea45fe2186bb22
Source dataset
uspto-grants-1999_04
Patent number
US05892094

Reaction notes

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