Methyl Acrylate → HCID 68843710, compound

HRID 860638Notes

Reaction equation

HRID 860638 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13](Br)=[C:12]([CH3:17])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[CH2:21].C(N(C(C)C)CC)(C)C>>[CH2:1]([O:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([CH:21]=[CH:20][C:19]([O:23][CH3:24])=[O:22])=[C:12]([CH3:17])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7294Methyl AcrylateHCID 81531DiisopropylethylamineHCID 57431984HCID 57431984, compound

Product 1

HCID 68843710HCID 68843710, compoundYield 84.7%

Conditions

Temperature
110 °C

Procedure

To a solution of 4-bromo-3-methyl-benzoic acid benzyl ester (36 g, 118 mmol) in propronitrile (1000 mL) is added methyl acrylate (43.3 mL) and diisopropylethyl amine (42 mL), the solution is degassed and filled with nitrogen for three times. To this mixture are added tri-o-tolyl-phosphane (14.5 g) and palladium acetate (5.34 g) under nitrogen, then heated at 110° C. overnight, cooled to room temperature, filtered through celite. The solvent is evaporated, the residue is taken into ethyl acetate and washed with water and brine, dried over sodium sulfate. Concentration and column chromatography on silica gel eluted with hexanes and ethyl acetate gave the title compound (31 g, 84.7%).

Workup

  1. customthe solution is degassed
  2. additionfilled with nitrogen for three times
  3. additionTo this mixture are added tri-o-tolyl-phosphane (14.5 g) and palladium acetate (5.34 g) under nitrogen
  4. temperaturecooled to room temperature
  5. filtrationfiltered through celite
  6. customThe solvent is evaporated
  7. washwashed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationConcentration and column chromatography on silica gel
  10. washeluted with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-c5bd7b54ff71406b9066f2652e4a1044
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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