Toluene → 5-Methoxy-[1,1'-biphenyl]-3-carbonitrile

HRID 539456Notes

Reaction equation

HRID 539456 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[C:5]#[N:6].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(OCC)(=O)C>[CH3:11][O:10][C:8]1[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 250673623-Bromo-5-methoxybenzonitrile

Product 1

HCID 706544735-Methoxy-[1,1'-biphenyl]-3-carbonitrileYield 91.7%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-bromo-5-methoxybenzonitrile (8.3 g, 39.1 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (S-Phos) (1.286 g, 3.13 mmol), phenylboronic acid (5.84 g, 47.0 mmol), Pd2(dba)3 and 200 mL toluene were charged in a flask and refluxed overnight. The reaction was cooled down and 200 mL of ethyl acetate was added. The crude mixture was run though a silica gel plug, and the product was confirmed by GC. After distillation under vacuum, 7.5 g of a white product was obtained.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction was cooled down
  3. distillationAfter distillation under vacuum

Sources & evidence

ORD record
ord-d498e7d55f294cc1931146d566d34271
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

Loading…