Methyl 4-bromo-3,5-dimethoxybenzoate → Methyl 4-[1-(ethoxy)ethenyl]-3,5-dimethoxybenzoate

HRID 1096987Notes

Reaction equation

HRID 1096987 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:14][CH3:15])[C:12]=1Br)[C:6]([O:8][CH3:9])=[O:7].[F-].[K+].[CH2:18]([O:20][C:21]([Sn](CCCC)(CCCC)CCCC)=[CH2:22])[CH3:19]>C1(C)C=CC=CC=1.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>[CH2:21]([O:20][C:18]([C:12]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[O:14][CH3:15])=[CH2:19])[CH3:22]

Participants

6

Reactant 3

HCID 117713Methyl 4-bromo-3,5-dimethoxybenzoateHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

Product 1

HCID 57930895Methyl 4-[1-(ethoxy)ethenyl]-3,5-dimethoxybenzoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Methyl 3,5-dimethoxy-4-bromobenzoate (500 mg) was dissolved in toluene in a nitrogen atmosphere, and 1-ethoxyvinyltributyltin (742 μL) and tetrakis(triphenylphosphine)palladium (211 mg) were added to it, and stirred overnight at 110° C. The reaction liquid was cooled to room temperature, then aqueous potassium fluoride solution was added to it, and stirred at room temperature. The reaction liquid was filtered through Celite, the Celite was washed with ethyl acetate, and the filtrate was washed with saturated saline water. The organic layer was dried with sodium sulfate, the sodium sulfate was removed through filtration, the filtrate was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 85/15) to obtain the title compound.

Workup

  1. additionwere added to it
  2. customThe reaction liquid
  3. temperaturewas cooled to room temperature
  4. stirringstirred at room temperature
  5. customThe reaction liquid
  6. filtrationwas filtered through Celite
  7. washthe Celite was washed with ethyl acetate
  8. washthe filtrate was washed with saturated saline water
  9. dry with materialThe organic layer was dried with sodium sulfate
  10. customthe sodium sulfate was removed through filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 85/15)

Sources & evidence

ORD record
ord-1c77621153e84b4ca2a4d1031262b5fe
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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