1036731-14-2

Upstream product

• 100-63-0 phenylhydrazine 
• 103-26-4 methyl cinnamate 
• 13370-06-4 1,5-diphenyl-3-hydroxy-1H-pyrazole 
• 6118-95-2 1,5-diphenylpyrazolidin-3-one 
• 1246513-41-6 ethyl 2-(1,5-diphenyl-1H-pyrazol-3-yloxy)acetate 

Relevant academic research and scientific papers

DMF-catalyzed direct and regioselective C-H functionalization: Electrophilic/nucleophilic 4-halogenation of 3-oxypyrazoles

A novel, straightforward, and highly regioselective 4-chlorination of 3-oxypyrazole derivatives in boiling thionyl chloride (SOCl2) in the presence of catalytic N,N-dimethylformamide (DMF) has been developed. This reaction likely proceeds through a DMF-catalyzed electrophilic/nucleophilic chlorination mechanism and involves electrophilic attack by SOCl2 and nucleophilic substitution by Cl- as the key steps. Based on this mechanism, the corresponding 4-bromination and 4-iodination of 3-oxypyrazoles have also been achieved in good yield by adding Br- and I -, respectively, to the reaction system. This halogenation method enables quick access to many original 4-halo-3-oxypyrazole series. A novel DMF-catalyzed electrophilic/nucleophilic 4-halogenation of 3-oxypyrazole derivatives has been developed. This halogenation procedure provides quick access to many novel 4-halo-3-oxypyrazole series.