Process for the Kumada coupling reaction

Details Process for the Kumada coupling reaction Process for the Kumada coupling reaction

2007-04-17

2007-04-17

Lambkin, Deborah C. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S081000, C549S083000

Reexamination Certificate

active

11033573

ABSTRACT:
A method for the formation of 3-alkylthiophenes or 3-arylthiophenes from 3-halothiophenes. More particularly, improvements on the Kumada coupling reaction for the production of 3-alkylthiophenes or 3-arylthiophenes by reacting a 3-halothiophene with an alkylmagnesiumhalide or arylmagnesiumhalide Grignard reagent in the presence of a catalyst and a 2-methyl tetrahydrofuran solvent. The 2-methyl tetrahydrofuran solvent allows for higher concentrations of the Grignard reagent with minimal or no dithienyl side product generation, achieving higher product yields and at a lower cost than other known methods.

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Tamao, K., et al. “Nickel-Phosphine Complex-Catalyzed Grignard Coupling-II.” Tetrahedron Vo. 38, No. 22, pp. 3347-3354. Feb. 9, 1982.

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