Water → 538-65-8

HRID 241317Notes

Reaction equation

HRID 241317 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+].Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O>[C:17]1(/[CH:3]=[CH:2]/[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7961BromobenzeneHCID 8846Butyl AcrylateHCID 11430Potassium Carbonate

Product 1

HCID 5273465538-65-8Yield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.38 g (2.9 mmol) of butyl acrylate and 0.30 g (2.2 mmol) of K2CO3 are added to a solution of 0.32 g (2.0 mmol) of bromobenzene in 20 ml of dimethylformamide. After the mixture has been stirred at room temperature for 5 minutes, 0.08 g (0.05 mmol) of [{Pd[P(C2F5)2O]2H}2(μ-Cl)2], prepared in accordance with Example 13, is added, and the reaction mixture is heated under reflux for 20 hours. After cooling and addition of 100 ml of water, the reaction mixture is extracted with 100 ml of diethyl ether. The organic phase is washed with water and dried using MgSO4. After filtration and removal of the solvent (in vacuo), 0.26 g of butyl (E)-3-(phenyl)acrylate is isolated as a colourless oil. The yield is 64%, based on the bromobenzene employed.

Workup

  1. additionis added
  2. temperaturethe reaction mixture is heated
  3. temperatureunder reflux for 20 hours
  4. temperatureAfter cooling
  5. extractionthe reaction mixture is extracted with 100 ml of diethyl ether
  6. washThe organic phase is washed with water
  7. customdried
  8. filtrationAfter filtration and removal of the solvent (in vacuo)

Sources & evidence

ORD record
ord-b6462be693e244c6964e0bf176e8f737
Source dataset
uspto-grants-2014_02
Patent number
US08648202B2

Reaction notes

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