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

HRID 1422365Notes

Reaction equation

HRID 1422365 reaction equation
CC(Cl)c1ccccc1.COc1ccc(/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>COc1ccc(/C=C/[C@H](C)c2ccccc2)cc1

Participants

7

Reactant 2

HCID 12648(1-Chloroethyl)benzeneHCID 5355683(E)-1-(2-Bromovinyl)-4-methoxybenzene

Product 1

HCID 1022299251-methoxy-4-[(E,3S)-3-phenylbut-1-enyl]benzeneYield 84%

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-76ac76ddff4041c5b4e05ca3d58f7db5
Source dataset
Electroreductive Coupling of Alkenyl and Benzyl Halides
Original link
View source

Reaction notes

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