Hydrogen Peroxide → 2-Cyano-4'-methylbiphenyl

HRID 1769193Notes

Reaction equation

HRID 1769193 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].OO>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C.C1(C)C=CC=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 162722-BromobenzonitrileHCID 79799Tolylboronic acid

Product 1

HCID 1455122-Cyano-4'-methylbiphenyl

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Equimolar amounts of 2-bromobenzonitrile and 4-methylphenylboronic acid are combined with tetrakis[triphenylphosphine] palladium, toluene, sodium carbonate and ethanol and refluxed vigorously, with stirring for 6 to 12 hours, preferably overnight. The mixture is allowed to cool to 10° to 30° C., preferably ambient temperature and hydrogen peroxide is added. The mixture is stirred, extracted with ether, washed with water, and dried over magnesium sulphate to produce an oil, 4-methyl-2'-cyanobiphenyl, a compound of Formula (35. To this oil, equimolar amounts of N-bromosuccinimide and azaisobutylnitrile are added, in a nonpolar solvent (such as ether, cyclohexane, or carbon tetrachloride; preferably carbon tetrachloride), and the mixture is heated under reflux for 1 to 4 hours, preferably 2 hours. The mixture is cooled and filtered, and the solvent is extracted to yield 4-(bromomethyl)-2'-cyanobiphenyl.

Workup

  1. temperaturerefluxed vigorously
  2. stirringThe mixture is stirred
  3. extractionextracted with ether
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-dbefd182a1fb49b59a048b6ea5d13b96
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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