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

HRID 443079Notes

Reaction equation

HRID 443079 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, Pt--C and sodium hydroxide 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 21.7 g of 4'-methyl-2-cyanobiphenyl having an LC purity of 98.1%.

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. filtrationPt--C and sodium hydroxide 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-b96230cb464a47da942f54da78cdf2e4
Source dataset
uspto-grants-1999_04
Patent number
US05892094

Reaction notes

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