Toluene → 2'-formylbiphenyl-2-carbonitrile

HRID 1769197Notes

Reaction equation

HRID 1769197 reaction equation
[B].Br[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-:19].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.O.C(O)C>[CH:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6])=[O:19]

Participants

10

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 162722-BromobenzonitrileHCID 5462311Boron

Product 1

HCID 2519652'-formylbiphenyl-2-carbonitrile

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The boron compound (24) (65.6 g) and 2-bromobenzonitrile (84 g) were placed into a 3 liter 3-neck flask fitted with a mechanical stirrer containing 20 g of tetrakis(triphenylphosphine)palladium(0), 1 liter of toluene, 480 ml of 2M sodium carbonate solution and 240 ml ethanol. The mixture was gently refluxed under argon with rapid stirring for 24 hours. A further 3 g of triphenylphosphine was added and the mixture was continued to reflux overnight. While it was still warm 200 ml of water and 300 ml of tetrahydrofuran was added to the mixture. The organic layer was separated while warm, and the aqueous layer was extracted with ethyl acetate. The organic extracts were combined and dried (MgSO4). The solid material was recrystallized from a mixture of ethyl acetate and methylene chloride, to yield 55 g of 2-formyl-2'-cyanobiphenyl (99+% pure).

Workup

  1. customfitted with a mechanical stirrer
  2. temperatureThe mixture was gently refluxed under argon
  3. temperatureto reflux overnight
  4. additionwas added to the mixture
  5. customThe organic layer was separated
  6. temperaturewhile warm
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. dry with materialdried (MgSO4)
  9. customThe solid material was recrystallized from a mixture of ethyl acetate and methylene chloride

Sources & evidence

ORD record
ord-7146cc9764a141a9a3db65396ac4b13f
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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