1-[(1R)-1-chloroethyl]-4-fluorobenzene → 1-fluoro-4-[(E,2S)-4-(4-methoxyphenyl)but-3-en-2-yl]benzene

HRID 1422378Notes

Reaction equation

HRID 1422378 reaction equation
COc1ccc(/C=C/Br)cc1.C[C@@H](Cl)c1ccc(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(F)cc2)cc1

Participants

7

Reactant 2

HCID 24659671-[(1R)-1-chloroethyl]-4-fluorobenzeneHCID 5355683(E)-1-(2-Bromovinyl)-4-methoxybenzene

Product 1

HCID 1664390441-fluoro-4-[(E,2S)-4-(4-methoxyphenyl)but-3-en-2-yl]benzeneYield 81%

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-81ca5303d7f14f0884fca3ce0db15f66
Source dataset
Electroreductive Coupling of Alkenyl and Benzyl Halides
Original link
View source

Reaction notes

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