Ethyl Acrylate → HCID 53401884, compound

HRID 1700422Notes

Reaction equation

HRID 1700422 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.CC(=O)OCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([CH:7]=1)[CH:13]=[CH:12][C:11]([O:15][CH2:16][CH3:17])=[O:14]

Participants

7

Reactant 3

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 5219352-Bromo-4-chloroanisole

Product 1

HCID 53401884HCID 53401884, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 10.6 g (48.2 mmol) of 2-bromo-4-chloroanisole in 30 ml of triethylamine was treated with 1 0.1 ml (81.2 mmol) of ethyl acrylate, 1.23 g of tri-o-tolylphosphine, and 0.45 g of palladium(II) acetate in an argon atmosphere. The reaction mixture was stirred at 100° C. for 2 days, then diluted with EA and filtered through Celite. The filtrate was washed with 1 N HCl and saturated NaCl solution, dried over Na2SO4, and concentrated. After chromatographic purification over SiO2 using EA/heptane (1:8) as an eluent, 0.85 g of the title compound resulted as a pale yellow oil.

Workup

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with 1 N HCl and saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customAfter chromatographic purification over SiO2

Sources & evidence

ORD record
ord-1aaae324d2074c5d80671cbe245599de
Source dataset
uspto-grants-2002_02
Patent number
US06350778B1

Reaction notes

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