138871-01-9

Upstream product

• 1842-26-8 (2-fluorophenyl)trimethylsilane 
• 367-11-3 ortho-difluorobenzene 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 574755-30-9 2-(2,3-difluoro-4-trimethylsilylphenyl)-5,5-dimethyl[1,3,2]dioxaborinane 
• 1417331-34-0 methyl 4-amino-6-(4-bromo-2,3-difluorophenyl)-5-fluoro-3-methoxypicolinate 
• 1417331-30-6 methyl 4-amino-6-(2,3-difluoro-4-(trimethylsilyl)phenyl)-5-fluoro-3-methoxypicolinate 
• 1417332-36-5 (2,3-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)trimethylsilane 

Relevant academic research and scientific papers

Fluorodesilylations of fluorophenyltrimethylsilanes with elemental fluorine: Discovery of a novel 1,2-migration of the trimethylsilyl group

The main product in the direct elemental fluorination of 4-fluorophenyltrimethylsilane was 1,4-difluorobenzene, produced by the ipso electrophilic substitution of the trimethylsilyl group. An unexpected product, 2,5-difluorophenyltrimethylsilane, was also formed as the result of a novel 1,2-migration of the trimethylsilyl group. The same trimethylsilyl 1,2-shifts were observed in the elemental fluorinations of 2-fluoro-and 2,4-difluoro-phenyltrimethylsilanes. We propose that the carbocations formed in the rearrangements were stabilised by the mescineric effect of the α-fluorine and the greater stability of these intermediates provided the driving force for the trimethylsilyl group migrations. Although the main products in all of the fluorinations were the fluorodesilylated product, the reactions were not totally regioselective and some competing fluorodeprotonation also occurred in the reactions of 2-fluoro-and 2,4-difluoro-phenyltrimethylsilanes. The role of protic acids and Lewis acids in particular triflic acid, trifluoroacetic acid and boron trifluoride in a variety of co-solvents, respectively, was crucial in all the fluorinations we studied, experiments done in their absence gave very poor yields. Optimal conditions for fluorination of silylated substrates are described.

Remote trimethylsilyl groups interfering with the ortho deprotonation of fluoroarenes and chloroarenes

(2-Fluorophenyl)trimethylsilane (2-F) and (2-chlorophenyl)-trimethylsilane (2-Cl) react with sec-butyllithium or lithium 2,2,6,6-tetramethylpiperidide under permutational hydrogen/metal interconversion (metalation) more slowly than, respectively, the corr

Process for the preparation of ring compounds

In a process for the preparation of ring compounds via a combinatorial synthesis, the reaction procedure is based on a Suzuki coupling, subsequent halo-demetallation and finally a further Suzuki coupling. The Suzuki couplings are each carried out with a boronic acid or a boronic acid ester. The reaction procedure uses provides novel ring compounds and uses novel synthesis units used for this purpose. The novel ring compounds are suitable for use as constituents in liquid-crystalline mixtures.

Combinatorial organic materials research (COMR): design, synthesis and screening of a 225-membered materials library of liquid crystalline fluorinated p-quaterphenyls

The rapid solution phase synthesis of novel liquid crystalline materials is demonstrated by utilising combinatorial and parallel methods for the preparation of a library of 225 differently fluorinated 4,4?-dipropyl-p-quaterphenyl. Chemical diversity was i

Process for the reaction of halogenated aromatics with electrophiles

The invention relates to a process for the reaction of fluorinated or chlorinated aromatics with electrophiles at the ortho position relative to the fluorine or chlorine atom, characterized in that a strong base is added to a mixture of the fluorinated or