Allyl bromide → 1-Ferrocenyl-I-methyl-1,3-butadiene

HRID 433008Notes

Reaction equation

HRID 433008 reaction equation
[Mg].[CH3:2][C:3]([C-:5]1C=C[CH:7]=[CH:6]1)=O.[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15].C(Br)C=C.C[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C1COCC1>[C-:10]1([C:6]([CH3:7])=[CH:5][CH:3]=[CH2:2])[CH:14]=[CH:13][CH:12]=[CH:11]1.[CH-:21]1[CH:22]=[CH:23][CH:24]=[CH:25]1.[Fe+2:15]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8058Hexane2×HCID 5462224Magnesium2×HCID 178466060HCID 178466060, compound

Product 1

HCID 1317224791-Ferrocenyl-I-methyl-1,3-butadieneYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

72 mg (3.0 mmole) of magnesium metal was placed in a 50 ml round bottom flask. 228 mg (1.0 mmole) of ferrocenyl methyl ketone and 181.5 mg (1.5 mmole) of allyl bromide were dissolved in 15 ml of THF. The resulting mixture was poured into the round bottom flask containing the magnesium metal while stirring at room temperature for two hours. After two-hour stirring, the cover of the flask was opened, and the liquid portion of the reaction mixture was introduced into a silica gel column, which had been wetted with n-hexane. All the liquid migrated into the silica gel, and the column was placed still for 24 hours. Next, the column was eluated with n-hexane. After evaporating the solvent from the eluate collected from the elution, 230 mg (0.91 mmole) of a purified title product was obtained with a yield of 91%.

Workup

  1. additionThe resulting mixture was poured into the round bottom flask
  2. stirringAfter two-hour stirring
  3. additionthe liquid portion of the reaction mixture was introduced into a silica gel column, which
  4. waitAll the liquid migrated into the silica gel, and the column was placed still for 24 hours
  5. customAfter evaporating the solvent from the
  6. customeluate collected from the elution, 230 mg (0.91 mmole) of
  7. customa purified title product
  8. customwas obtained with a yield of 91%

Sources & evidence

ORD record
ord-8fd3d17a05024ca185d17019e7633416
Source dataset
uspto-grants-2003_12
Patent number
US06664409B1

Reaction notes

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