Ethyl Acetate → Ethyl 2-(3-vinylphenyl)acetate

HRID 924992Notes

Reaction equation

HRID 924992 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH2:14]([Sn](CCCC)(CCCC)C=C)[CH2:15]CC.CCOC(C)=O>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:14]([C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1)=[CH2:15]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 11470552Ethyl 3-(bromophenyl)acetate

Product 1

HCID 11687033Ethyl 2-(3-vinylphenyl)acetateYield 54%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of ethyl 2-(3-bromophenyl)acetate (1.5 g, 6.1 mmol) in anhydrous DMF (15 mL) was added tributyl(vinyl)stannane (2.1 mL, 7.4 mmol) and tetrakis(triphenylphosphine) palladium (400 mg, 0.5 mmol) under nitrogen atmosphere. The resulting mixture was stirred at 110° C. for 8 hours. Followed a standard aqueous/EtOAc workup. Purified by silica gel column chromatography (petroleum:ether/ethyl acetate=15:1) (640 mg, yield 54%).

Workup

  1. customPurified by silica gel column chromatography (petroleum:ether/ethyl acetate=15:1) (640 mg, yield 54%)

Sources & evidence

ORD record
ord-7ca8bd98bdca4d04996787da4cd92007
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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