Lithium Bromide → 1-(4-Bromo-2-phenyl-1-cyclopenten-1-yl)benzene

HRID 2416409Notes

Reaction equation

HRID 2416409 reaction equation
[C:1]1([C:7]2[CH2:8][CH:9](S(Cl)(=O)=O)[CH2:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[Br-:23]>CC(C)=O>[Br:23][CH:9]1[CH2:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 223232413,4-Diphenyl-3-cyclopentene-1-sulfonyl chloride

Product 1

HCID 223232201-(4-Bromo-2-phenyl-1-cyclopenten-1-yl)benzeneYield 82.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3,4-diphenyl-3-cyclopentene-1-sulfonyl chloride (4 g) and 3 g of LiBr was added 70 mL of acetone. Reaction mixture was stirred under reflux for 2.5 hr. Solvent was removed under reduced pressure and the residue was extracted with 60 mL of methylene chloride. Solution was filtered and solvent was removed under reduced pressure giving 3.1 g of product as brown-yellow solid.

Workup

  1. customReaction mixture
  2. temperatureunder reflux for 2.5 hr
  3. customSolvent was removed under reduced pressure
  4. extractionthe residue was extracted with 60 mL of methylene chloride
  5. filtrationSolution was filtered
  6. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c6ed9bea1f5c4cc9959f048566ffdb48
Source dataset
uspto-grants-2004_11
Patent number
US06825147B2

Reaction notes

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