Bis(eta-cyclopentadienyl) iron → HCID 178520645, compound

HRID 259288

Reaction equation

HRID 259288 reaction equation
[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[Fe+2:11].[Cl:12][CH2:13][CH2:14][C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Cl:12][CH2:13][CH2:14][C:15]([C-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)=[O:16].[CH-:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[Fe+2:11]

Participants

5

Reactant 3

HCID 7611Bis(eta-cyclopentadienyl) ironHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178520645HCID 178520645, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ferrocene (2.63 kg, 14.2 mole) and 3-chloropropionyl chloride (1.8 kg, 15.6 moles) in dry dichloromethane (23.5 l) was cooled to -3° and treated over 1 hour with aluminium chloride (2.08 kg, 15.6 mole). The reaction mixture was left to stir for 2 hours. To this was then added ice water (30 kg) and the two layers separated. The aqueous layer was washed with dichloromethane and the combined organic liquors were washed with water (30 l), 2% aqueous sodium bicarbonate solution (20 l) and water again (60 l). The organic liquors were then dried and concentrated affording black/brown semi-solid chloropropionyl ferrocene (3.5 kg).

Workup

  1. waitThe reaction mixture was left
  2. customadded ice water (30 kg) and the two layers separated
  3. washThe aqueous layer was washed with dichloromethane
  4. washthe combined organic liquors were washed with water (30 l), 2% aqueous sodium bicarbonate solution (20 l) and water again (60 l)
  5. customThe organic liquors were then dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ad264747c90646f39039de9bd0e79dc8
Source dataset
uspto-grants-1977_07
Patent number
US04036983

Linked notes

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