426207-59-2

Upstream product

• 75-62-7 Bromotrichloromethane 
• 1571-08-0 methyl 4-formylbenzoate 
• 96349-60-9 4-(2,2,2-Trichloro-1-hydroxy-ethyl)-benzoic acid methyl ester 

Downstream Products

• 934372-11-9 (Z)-2-chloro-1-(4-methoxycarbonylphenyl)-5-phenylpent-1-ene 
• 1256954-53-6 (Z)-methyl 4-(3-(benzyloxy)-2-chloro-3-oxoprop-1-enyl)benzoate 

Relevant academic research and scientific papers

The use of bromotrichloromethane in chlorination reactions

Carbon tetrachloride is no longer used as a common solvent due to its toxicity and harmful environmental impact. The synthesis of gem-dichloroalkenes from aldehydes by using triphenylphosphine typically requires carbon tetrachloride as a solvent. We report that stoichiometric bromotrichloromethane in acetonitrile can be used in place of solvent quantities of carbon tetrachloride in this transformation. Similarly, bromotrichloromethane in dichloromethane can be used for the room-temperature Appel reaction of benzyl alcohols to form benzyl chlorides, which is commonly carried out in refluxing carbon tetrachloride. Georg Thieme Verlag Stuttgart New York.

Suzuki-Miyaura cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN

We addressed an unexplored application of the Suzuki-Miyaura protocol to the cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN. The use of bisphosphine ligands with a large P-Pd-P bite angle allowed us to synthesize Z-chlorinated internal alkenes in good yields resulting from a selective monocoupling process, a recurrent challenge with 1,1-dichloro-1-alkenes. Moreover, these monochlorinated olefins could be further transformed providing stereospecifically trisubstituted olefins.