Potassium Carbonate → 2'-(Cyanomethyl)-1,1'-biphenyl-4-carboxylic acid

HRID 2244221Notes

Reaction equation

HRID 2244221 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[C:11]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)([OH:13])=[O:12].C(=O)([O-])[O-].[K+].[K+]>O.O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:9]([CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:17]1[CH:18]=[CH:19][C:14]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=1)#[N:10]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 296252-Bromobenzyl cyanideHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 686894952'-(Cyanomethyl)-1,1'-biphenyl-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture containing 5.88 g (0.03 mol) of (2-bromo-phenyl)-acetonitrile, 4.978 g. (0.03 mol) of 4-carboxyphenylboronic acid, 8.29 g (0.06 mol) of potassium carbonate and 0.52 g of dichlorobis(triphenylphosphine)palladium(II) in 46 mL of water and 25 mL of 1,4-dioxane was heated under reflux for two hours in an atmosphere of nitrogen. The reaction mixture was allowed to cool to room temperature and filtered. The dioxane was removed in vacuo and the residue diluted with 100 mL of water and then acidified with 20% hydrochloric acid. The crude product (1.2g) was recrystallized from ethanol to give a solid, m.p. 218-220° C.

Workup

  1. temperatureunder reflux for two hours in an atmosphere of nitrogen
  2. filtrationfiltered
  3. customThe dioxane was removed in vacuo
  4. additionthe residue diluted with 100 mL of water
  5. customThe crude product (1.2g) was recrystallized from ethanol
  6. customto give a solid, m.p. 218-220° C.

Sources & evidence

ORD record
ord-f72d789be689497c97e008fdb4f84f4b
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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