Potassium Iodide → [1,1'-Biphenyl]-4-carbonitrile, 4'-(decyloxy)-

HRID 651310

Reaction equation

HRID 651310 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[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 112405[1,1'-Biphenyl]-4-carbonitrile, 4'-(decyloxy)-

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-cyano-4′-hydroxybiphenyl (56) (10.10 g, 0.052 mol), 1-bromodecane (14.38 g, 0.065 mol), anhydrous potassium carbonate (37.32 g, 0.27 mol), butanone (300 ml) and a trace of potassium iodide was heated under reflux overnight. The cooled solution was filtered to remove inorganic salts and the solvent was removed in vacuo. The residual oil was distilled (to remove excess bromide) and finally purified by column chromatography (dichloromethane) to yield a colourless, low melting solid.

Workup

  1. temperatureunder reflux overnight
  2. filtrationThe cooled solution was filtered
  3. customto remove inorganic salts
  4. customthe solvent was removed in vacuo
  5. distillationThe residual oil was distilled
  6. custom(to remove excess bromide)
  7. customfinally purified by column chromatography (dichloromethane)
  8. customto yield a colourless,

Sources & evidence

ORD record
ord-32777e1a215a4a0dac166d894cb7b24c
Source dataset
uspto-grants-2001_08
Patent number
US06278028B1

Linked notes

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