(E)-1-(2-Bromovinyl)-4-methoxybenzene → 1-methoxy-4-[(E,3S)-3-[4-(trifluoromethyl)phenyl]but-1-enyl]benzene

HRID 1422381Notes

Reaction equation

HRID 1422381 reaction equation
COc1ccc(/C=C/Br)cc1.C[C@@H](Cl)c1ccc(C(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(C(F)(F)F)cc2)cc1

Participants

7

Reactant 2

HCID 5355683(E)-1-(2-Bromovinyl)-4-methoxybenzeneHCID 524305171-[(1R)-1-chloroethyl]-4-(trifluoromethyl)benzene

Product 1

HCID 1624024041-methoxy-4-[(E,3S)-3-[4-(trifluoromethyl)phenyl]but-1-enyl]benzeneYield 55%

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-a405dd8472064079a9c5d05c0b13dd12
Source dataset
Electroreductive Coupling of Alkenyl and Benzyl Halides
Original link
View source

Reaction notes

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