Methanol → 2-Cyano-4'-methylbiphenyl

HRID 1614780Notes

Reaction equation

HRID 1614780 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.Br[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[C:20]#[N:21].CO>[Pd](Cl)Cl.C1(C)C=CC=CC=1>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:18]2[C:19]([C:20]#[N:21])=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 162722-BromobenzonitrileHCID 79799Tolylboronic acid

Product 1

HCID 1455122-Cyano-4'-methylbiphenylYield 85.4%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 1140TolueneSolvent

Procedure

2M Sodium carbonate solution (200 ml) was added to a stirred mixture of 4-methylphenylboronic acid (30 g), 2-bromobenzonitrile (36.4 g), palladium (II) chloride (0.4 g), methanol (200 ml) and toluene (200 ml) at 5° C. The temperature rose to approximately 20° C. and a solid precipitated. The reaction mixture was then heated at reflux for 2 hours. The reaction mixture was allowed to cool and water (100 ml) was added, followed by diatomaceous earth (5 g). The mixture was stirred for 15 minutes, then filtered through diatomaceous earth. The organic phase of the filtrate was separated and washed with 2M sodium carbonate solution and then water. The organic phase was then filtered and the filtrate evaporated. The resultant solid was recrystallised from petroleum ether (b.p. 110°-120° C.) to give 4'-methylbiphenyl-2-carbonitrile (33 g) which was used without further purification.

Workup

  1. customrose to approximately 20° C.
  2. customa solid precipitated
  3. temperatureThe reaction mixture was then heated
  4. temperatureat reflux for 2 hours
  5. temperatureto cool
  6. additionwater (100 ml) was added
  7. filtrationfiltered through diatomaceous earth
  8. customThe organic phase of the filtrate was separated
  9. washwashed with 2M sodium carbonate solution
  10. filtrationThe organic phase was then filtered
  11. customthe filtrate evaporated
  12. customThe resultant solid was recrystallised from petroleum ether (b.p. 110°-120° C.)

Sources & evidence

ORD record
ord-6ccfeab3b9604b9a92fc9f2b0fd8fd16
Source dataset
uspto-grants-1993_03
Patent number
US05198439

Reaction notes

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