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

HRID 2178086Notes

Reaction equation

HRID 2178086 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-9420e8e099af4cae8a561daa88620e7b
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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