Allyl bromide → Phenyl-ferrocenyl-butadien

HRID 322846

Reaction equation

HRID 322846 reaction equation
[Sm].ICCI.[I-].[I-].[Sm+2].[C:9]([C-:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1)(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH-:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1.[Fe+2:27].C(Br)C=C>O1CCCC1>[C-:17]1([C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:26][CH:22]=[CH2:23])[CH:21]=[CH:20][CH:19]=[CH:18]1.[CH-:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1.[Fe+2:27]

Participants

7

Reactant 5

HCID 7841Allyl bromideHCID 122241,2-DiiodoethaneHCID 23951SamariumHCID 176468997Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(phenyl)methanone;iron(2+)HCID 178506586HCID 178506586, compound

Product 1

HCID 129629832Phenyl-ferrocenyl-butadienYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a nitrogen environment, about 330 mg (2.20 mmole) of samarium and about 500 mg (1.77 mmole) of 1,2-diiodoethane is disposed in a round-bottomed flask. About 20 ml of tetrahydrofuran is added into the round-bottomed flask. The mixture in the round-bottomed flask is stirred until a deep-blue samarium diiodide solution is obtained. Following the process flow described in Example 1, about 348 mg (1.20 mmole) of benzoylferrocene reacts with about 242 mg (2.0 mmole) of allyl bromide to produce oil-type 1-Ferrocenyl-1-phenyl-1,3-butadiene (3c) with a weight of about 373 mg (1.19 mmole) and a yield of about 99%.

Workup

  1. customis obtained

Sources & evidence

ORD record
ord-bbdbdb3bbb01451496fa2ee7abb17493
Source dataset
uspto-grants-2001_04
Patent number
US06211392B1

Linked notes

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