4-Bromo-2-chloro-1-ethenylbenzene → 4-Bromo-2-chloro-1-ethylbenzene

HRID 70562Notes

Reaction equation

HRID 70562 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[C:4]([Cl:10])[CH:3]=1.[H][H]>O1CCCC1.C([O-])(=O)C.[Fe+2].C([O-])(=O)C.[Rh]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[C:4]([Cl:10])[CH:3]=1

Participants

6

Reactant 2

HCID 578427134-Bromo-2-chloro-1-ethenylbenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 536329144-Bromo-2-chloro-1-ethylbenzeneYield 46.5%

Reagents, catalysts & solvents 3

HCID 18344Ferrous acetateCatalystHCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-2-chloro-1-ethenylbenzene (883 mg), iron(II) acetate (7 mg) and 5% rhodium-activated carbon (167 mg) in tetrahydrofuran (17 mL) was stirred at room temperature for three hours in a hydrogen atmosphere. The reaction solution was filtered through celite and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only) to give the title compound as a colorless oil (414 mg, 46%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane only)

Sources & evidence

ORD record
ord-10712600b2644c84864e7dd74dc673eb
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…