Synthesis of 1,2-bis(trimethylsilyl)benzene derivatives from 1,2-dichlorobenzenes using a hybrid metal Mg/CuCl in the presence of LiCl in 1,3-dimethyl-2-imidazolidinone.

Synthesis of 1,2-bis(trimethylsilyl)benzene derivatives from 1,2-dichlorobenzenes using a hybrid metal Mg/CuCl in the presence of LiCl in 1,3-dimethyl-2-imidazolidinone.

The Journal of organic chemistry (2013-03-20)

Tsugio Kitamura, Keisuke Gondo, Toshimasa Katagiri

ABSTRACT

A practical and safe synthesis of 1,2-bis(trimethylsilyl)benzene from 1,2-dichlorobenzene and Me3SiCl was achieved by use of a hybrid metal of Mg and CuCl in the presence of LiCl in 1,3-dimethyl-2-imidazolidinone (DMI). This method does not require a toxic HMPA, provides a high yield of the product under mild conditions, and is also applied to synthesis of substituted 1,2-bis(trimethylsilyl)benzenes and poly(trimethylsilyl)benzenes.

MATERIALS

Product Number

Brand

Product Description

193453

Sigma-Aldrich

1,3-Dimethyl-2-imidazolidinone, reagent grade

40727

Sigma-Aldrich

1,3-Dimethyl-2-imidazolidinone, ≥99.0% (GC)

40725

Sigma-Aldrich

1,3-Dimethyl-2-imidazolidinone, absolute, over molecular sieve (H₂O ≤0.04%), ≥99.5% (GC)