Allyl bromide → 1,3-Butadienylferrocene

HRID 433007

Reaction equation

HRID 433007 reaction equation
[C-:1]1(C=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-]1C=CC=C1.[Fe+2:13].CC([C-]1C=CC=C1)=O.[CH-]1C=CC=C1.[Fe+2].C(Br)C=C.[C-:32]1([CH:37](O)[CH2:38][CH:39]=[CH2:40])[CH:36]=[CH:35][CH:34]=[CH:33]1.[CH-]1C=CC=C1.[Fe+2]>CCOCC.[Mg]>[C-:32]1([CH:37]=[CH:38][CH:39]=[CH2:40])[CH:36]=[CH:35][CH:34]=[CH:33]1.[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Fe+2:13]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 15184314FerrocenecarboxyaldehydeHCID 178450094HCID 178450094, compoundHCID 178466060HCID 178466060, compound

Product 1

HCID 1296652321,3-Butadienylferrocene

Reagents, catalysts & solvents 2

HCID 5462224MagnesiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

Ferrocenaldehyde or ferrocenyl methyl ketone and allyl bromide are reacted in an ether solvent and in the presence of magnesium metal as a catalyst. The liquid portion of the reaction mixture is introduced into a silica gel column, wherein the weak acidity of the silica gel is able to dehydrate the reaction intermediate 1-ferrocenyl-3-buten-1-ol product. The column is eluted with n-hexane, and after evaporating the solvent from the eluate collected, a purified ferrocenyl-1,3-butadiene product is obtained.

Workup

  1. additionThe liquid portion of the reaction mixture is introduced into a silica gel column, wherein the weak acidity of the silica gel
  2. washThe column is eluted with n-hexane
  3. customafter evaporating the solvent from the eluate collected

Sources & evidence

ORD record
ord-1873e47b27344b03a5faf5cb04c75af6
Source dataset
uspto-grants-2003_12
Patent number
US06664409B1

Linked notes

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