Isopropenyl acetate → HCID 66770339, compound

HRID 1039856Notes

Reaction equation

HRID 1039856 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.C[O-].C([Sn+](CCCC)CCCC)CCC.C([O:29][C:30]([CH3:32])=[CH2:31])(=O)C.[F-].[K+]>C1(C)C=CC=CC=1.O.[Cl-].[Na+].O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CCOC(C)=O>[O:29]=[C:30]([CH3:32])[CH2:31][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1

Participants

11

Reactant 4

HCID 7916Isopropenyl acetateHCID 36023(3-Bromophenyl)acetonitrileHCID 522689Potassium FluorideHCID 11964040Methoxytri-n-butylstannane

Product 1

HCID 66770339HCID 66770339, compoundYield 69.1%

Reagents, catalysts & solvents 6

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A stirred solution of 3-bromophenylacetonitrile (10.0 g, 51.0 mmol), tributyltin methoxide (17.6 mL, 61.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (500 mg, 0.5 mmol), isopropenyl acetate (6.74 mL, 61.2 mmol) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (800 mg, 2 mmol) in toluene (100 mL, degassed) was heated at 100° C. under nitrogen for 6 h. The reaction mixture was cooled to room temperature and EtOAc (30 mL) was added. A solution of potassium fluoride (10 g, 200 mmol) in water (52 mL) was then added and the resulting mixture was stirred overnight. Brine was added and the mixture was filtered through a pad of Celite. The layers were separated and the organic layer was dried over sodium sulfate, filtered (cotton plug) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound (6.1 g, 69% yield) as a brown oil.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered (cotton plug)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b832cb931c7f4e708d34d8ac65ab09b3
Source dataset
uspto-grants-2013_10
Patent number
US08551978B2

Reaction notes

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