(E)-1-(2-Bromovinyl)-4-methoxybenzene → (3S)-1-(4-Methoxyphenyl)-3-[4-(trifluoromethoxy)phenyl]-1-butene

HRID 1422380Notes

Reaction equation

HRID 1422380 reaction equation
COc1ccc(/C=C/Br)cc1.C[C@@H](Cl)c1ccc(OC(F)(F)F)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)c2ccc(OC(F)(F)F)cc2)cc1

Participants

7

Reactant 2

HCID 5355683(E)-1-(2-Bromovinyl)-4-methoxybenzeneHCID 288986751-[(1R)-1-chloroethyl]-4-(trifluoromethoxy)benzene

Product 1

HCID 101899631(3S)-1-(4-Methoxyphenyl)-3-[4-(trifluoromethoxy)phenyl]-1-buteneYield 79%

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-48cb5430272f43a2b77d809fadf5f623
Source dataset
Electroreductive Coupling of Alkenyl and Benzyl Halides
Original link
View source

Reaction notes

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