Toluene → Methyl 3-(4-cyanobiphenylyl)acrylate

HRID 12992Notes

Reaction equation

HRID 12992 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[C:14](C1C=CC(B(O)O)=CC=1)#[N:15].CCOC(C)=O.[C:31]1(C)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CO.C([O-])([O-])=O.[Na+].[Na+].O.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>[C:14]([C:13]1[CH:2]=[CH:3][C:4]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])[CH:12]=1)#[N:15]

Participants

9

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 8167732-Propenoic acid, 3-(4-bromophenyl)-, methyl esterHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 68583491Methyl 3-(4-cyanobiphenylyl)acrylate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

820 mg (3.4 mmol) of methyl 4-bromocinnamate were dissolved in 7 ml of dry toluene, added with 116 mg (0.1 mmol) of Pd(PPh3)4, a solution of 374 mg (1.1 mmol) of 4-cyanobenzeneboronic acid in 2 ml of MeOH, 6.8 ml of 2M Na2CO3 in water, and refluxed 9 h. Addition of EtOAc, washing with water, then with brine, filtration and flash chromatography (Merck silicagel) with Hexane/EtOAc mixtures 9/1 gave 273 mg of methyl 3-(4-cyanobiphenylyl)acrylate, mp. 150-152° C.

Workup

  1. washwashing with water
  2. filtrationwith brine, filtration and flash chromatography (Merck silicagel) with Hexane/EtOAc

Sources & evidence

ORD record
ord-6c1398decc134fd89f74b9803ea17d10
Source dataset
uspto-grants-2010_06
Patent number
US07728039B2

Reaction notes

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