Benzyl Bromide → 4'-(Benzyloxy)[1,1'-biphenyl]-4-carbonitrile

HRID 1722609Notes

Reaction equation

HRID 1722609 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(#N)C>[CH2:23]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 200999334'-(Benzyloxy)[1,1'-biphenyl]-4-carbonitrileYield 84.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 250-ml, three-necked, roundbottom flask equipped with a magnetic stirrer, heating mantle, thermometer, and condenser were placed 1.76 g (9.0 mmol) 4-hydroxy-4'-biphenylcarbonitrile, 3.94 g (28.5 mmol) powdered anhydrous potassium carbonate, 1.18 ml (9.92 mmol) α-bromotoluene, and 150 ml acetonitrile. After stirring the mixture under reflux for two hours, TLC analysis showed that none of the phenolic starting material remained. Two-thirds of the acetonitrile was then distilled off, and 200 ml dichloromethane was added. The mixture was filtered through Celite and the solids were washed thoroughly with dichloromethane. Evaporation of the filtrate yielded white crystals which were purified by recrystallization from methanol. 2.17 g (84.4%) of product was obtained; mp 150°-151.5° C. The following structure was confirmed by infrared, nuclear magnetic resonance, and mass spectral analyses. ##STR24##

Workup

  1. customIn a 250-ml, three-necked, roundbottom flask equipped with a magnetic stirrer
  2. temperatureheating mantle
  3. customthermometer, and condenser were placed
  4. temperatureunder reflux for two hours
  5. distillationTwo-thirds of the acetonitrile was then distilled off
  6. addition200 ml dichloromethane was added
  7. filtrationThe mixture was filtered through Celite
  8. washthe solids were washed thoroughly with dichloromethane
  9. customEvaporation of the filtrate
  10. customyielded white crystals which
  11. customwere purified by recrystallization from methanol

Sources & evidence

ORD record
ord-916d293a937148cfb7dd6c0827ec406a
Source dataset
uspto-grants-1989_08
Patent number
US04857227

Reaction notes

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