Methyl Acrylate → HCID 13415097, compound

HRID 1062688Notes

Reaction equation

HRID 1062688 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].Br[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12].C([O-])(=O)C.[Na+].C1(C)C=CC(P(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([C:10]1[CH:9]=[C:8](/[CH:3]=[CH:2]/[C:1]([O:5][CH3:6])=[O:4])[CH:15]=[CH:14][CH:13]=1)#[N:12]

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 13956Phosphine, tris(4-methylphenyl)-HCID 233813-BromobenzonitrileHCID 517045Sodium Acetate

Product 1

HCID 13415097HCID 13415097, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

7.31 ml (74.5 mmol) of methyl acrylate, 13.6 g (74.5 mmol) of 3-bromobenzonitrile and 6.6 g (74.5 mmol) of sodium acetate are suspended in 100 ml of DMF and heated at 120° C. for 30 min until a clear solution has formed. Then a solution of 4.0 g of palladium acetate and 21.0 g of tri-p-tolylphosphine in 5 ml of DMF is added dropwise to the reaction solution, and the mixture is stirred at 120° C. for 2 h. The reaction solution is then diluted with 500 ml of water, and the resulting precipitate is filtered off with suction. Drying under high vacuum and recrystallization from ethyl acetate/petroleum ether result in 12.6 g of the title compound. The mass spectrum shows the molecular peak MH+ at 187.7 Da.

Workup

  1. customhas formed
  2. filtrationthe resulting precipitate is filtered off with suction
  3. dry with materialDrying under high vacuum and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-b5d2b23fcee34ad291125278c833d536
Source dataset
uspto-grants-2005_11
Patent number
US06962941B2

Reaction notes

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