(1-Chloroethyl)benzene → 4-[(E,3S)-3-phenylbut-1-enyl]benzonitrile

HRID 1422367Notes

Reaction equation

HRID 1422367 reaction equation
CC(Cl)c1ccccc1.N#Cc1ccc(/C=C/Br)cc1>CC(=O)N(C)C.COCCOC.[Cl][Ni][Cl].[I-].[Na+].c1ccc2c(c1)C[C@@H]1OC(C3(C4=N[C@@H]5c6ccccc6C[C@@H]5O4)CC3)=N[C@H]21>C[C@@H](/C=C/c1ccc(C#N)cc1)c1ccccc1

Participants

7

Reactant 2

HCID 12648(1-Chloroethyl)benzeneHCID 117458344-(2-Bromoethenyl)benzonitrile

Product 1

HCID 1021418044-[(E,3S)-3-phenylbut-1-enyl]benzonitrileYield 72%

Reagents, catalysts & solvents 4

HCID 5238Sodium IodideReagentHCID 11245230(3aR,3a'R,8aS,8a'S)-2,2'-(Cyclopropane-1,1-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole)CatalystHCID 15773433Dichloronickel;1,2-dimethoxyethaneCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Workup

  1. additionNo procedure recorded
  2. additionNo procedure recorded
  3. extractionKeep organic
  4. additionNo procedure recorded
  5. extractionKeep organic
  6. additionNo procedure recorded
  7. extractionKeep organic
  8. washNo procedure recorded
  9. dry with materialNo procedure recorded
  10. filtrationKeep filtrate
  11. concentrationNo procedure recorded

Sources & evidence

ORD record
ord-d31a21739b314cc7afcc8d2349e75056
Source dataset
Electroreductive Coupling of Alkenyl and Benzyl Halides
Original link
View source

Reaction notes

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