Bromide ion → 4-(4-Prop-2-enoxyphenyl)benzonitrile

HRID 490031Notes

Reaction equation

HRID 490031 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[Br-].C(=O)([O-])[O-].[K+].[K+].[CH3:23][C:24](=O)[CH2:25]C>O>[CH2:25]([O:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)=[CH:10][CH:11]=1)[CH:24]=[CH2:23]

Participants

6

Reactant 4

HCID 259Bromide ionHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 23419874-(4-Prop-2-enoxyphenyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture obtained by adding 20 g of 4-cyano-4′-hydroxybiphenyl, 20 g of ally bromide and 25 g of potassium carbonate to 250 mL of butanone was refluxed for 7 hours. Water was added to the reaction mixture, which was then separated. An organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain a residue, which was purified by silica gel column chromatography using toluene as an elusion solvent and then subjected to recrystallization from ethanol to obtain 22 g of 4-allyloxy-4′-cyanobiphenyl.

Workup

  1. customA reaction mixture obtained
  2. temperaturewas refluxed for 7 hours
  3. customwas then separated
  4. washAn organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customto obtain a residue, which
  8. customwas purified by silica gel column chromatography
  9. customsubjected to recrystallization from ethanol

Sources & evidence

ORD record
ord-f839fe5bb4354ca6ac278e5ae858b7ab
Source dataset
uspto-grants-2009_05
Patent number
US07527746B2

Reaction notes

Loading…