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Tributylvinyltin → 3-Methyl-4-vinylbenzonitrile

HRID 1250279
Notes
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Reaction equation

HRID 1250279 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[CH:11]([Sn](CCCC)(CCCC)CCCC)=[CH2:12]>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>[CH3:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[CH:11]=[CH2:12])[C:6]#[N:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 27374944-Bromo-3-methylbenzonitrile

Product 1

HCID 183278913-Methyl-4-vinylbenzonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

0.75 g (0.65 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to a solution of 5.1 g (0.026 mol) of 4-bromo-3-methylbenzonitrile and 8.3 g (0.026 mol) of vinyltributyltin in 250 mL of toluene under argon, and the reaction was heated at reflux overnight. The mixture was filtered through a layer of celite and evaporated. The residue was flash chromatographed on silica gel with heptane:EtOAc (1:1) as eluant. Yield: 4.0 g (100%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux overnight
  3. filtrationThe mixture was filtered through a layer of celite and
  4. customevaporated
  5. customchromatographed on silica gel with heptane:EtOAc (1:1) as eluant

Sources & evidence

ORD record
ord-49de23461ecc4f7091063c4777cfbca5
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06337394B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes