78152-53-1

Usage

InChI:InChI=1/C6H4Cl3N/c7-5-3-1-2-4(10-5)6(8)9/h1-3,6H

Upstream product

• 1929-82-4 nitrapyrin 
• 18368-63-3 6-chloro-2-picoline 
• 33674-97-4 6-chloro-2-pyridinemethanol 
• 96-36-6 methyl phosphite 
• 78846-88-5 6-chloro-2-chloromethylpyridine 

Downstream Products

• 82423-94-7 2-chloro-6-(diphenoxymethyl)pyridine 
• 82424-04-2 2-[Bis-(4-methoxyphenoxy)methyl]-6-(4-methoxyphenoxy)pyridine 

Relevant academic research and scientific papers

An equilibrium halogen transfer reaction with evidence for S(RN)1-like behavior

The 'reduction' of 2-chloro-6-(trichloromethyl)pyridine to the dichloromethyl derivative by chloroform under basic conditions yields carbon tetrachloride as a companion product. The reaction is demonstrated to be reversible and to have preparative value. Strong inhibition by electron capture agents and also strong acceleration by electron-donating agents is observed. The mechanistic interpretation is electron-transfer initiation followed by reversible radical chains to establish the equilibrium.

Efficient pyridinylmethyl functionalization: Synthesis of 10,10-bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (DMP 543), an acetylcholine release enhancing agent

2-Fluoro-4-methylpyridine (3) is efficiently functionalized by chlorination, hydrolysis and methane-sulfonylation into the novel alkylating agent 7. This mesylate is used for the bisalkylation of anthrone under carefully defined conditions to prepare the cognition enhancer drug candidate 1. This process proceeds in up to 37% overall yield and is adaptable for large scale synthesis.

Reduction of trichloromethylpyridines to dichloromethylpyridines

2(6)-(Trichloromethyl)pyridines are reduced to the corresponding 2(6)-(dichloromethyl)pyridines by treatment with a strong base and an anionic reductant derived from a reductant source material selected from the group consisting of dialkylphosphite and trialkylphosphite said treatment taking place in the presence of a polar, non-hydroxylic solvent and/or a phase transfer catalyst.

Preparation of (dichloromethyl) pyridines by reductive dechlorination

(Dichloromethyl) substituted pyridines are prepared from (trichloromethyl) substituted pyridines by the reaction thereof under reductive dechlorination conditions with metallic iron or a ferrous iron compound and an acid.