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Tributylvinyltin → Ethyl 2-(3-vinylphenyl)acetate

HRID 2971
Notes
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Reaction equation

HRID 2971 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.[CH:14]([Sn](CCCC)(CCCC)CCCC)=[CH2:15]>CN(C=O)C.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>[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]
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 11470552Ethyl 3-(bromophenyl)acetate

Product 1

HCID 11687033Ethyl 2-(3-vinylphenyl)acetate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.0 mmol of ethyl 3-bromophenylacetate, 1.5 mmol of vinyltributyltin, and 0.1 mmol of Pd(PPh3)4 in 4 mL DMF was stirred and heated at 90° C. for 1-16 h. Chromatography provided ethyl 3-vinylphenylacetate.

Sources & evidence

ORD record
ord-22f4a8336221412198601584d84cd4b1
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731432

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes