113195-47-4

Upstream product

• 1442-03-1 2-methylsulfanyl-benzoyl chloride 
• 19614-16-5 2-bromo-1-(methylsulfanyl)benzene 
• 693-02-7 hex-1-yne 
• 29541-98-8 pentylidenetriphenylphosphorane 
• 113195-40-7 1-(2-methylsulfanylbenzoyl)pentylidene(triphenyl)phosphorane 

Relevant academic research and scientific papers

Efficient synthesis of 3-benzoyl Benzo[b]thiophenes and raloxifene via Mercury(II)-Catalyzed cyclization of 2-alkynylphenyl alkyl sulfoxides

The unique selective estrogen receptor modulator, Raloxifene (1), and antitubulin agent 2 were synthesized through the key intermediate, 4-methoxybenzyl 2-bromo-4-methoxyphenyl sulfoxide (6), respectively. It was found that compared with the o-sulfanyl aryl bromides, the sulfinyl group at ortho position accelerated the Sonogashira coupling reaction of aryl bromides. Thus, compound 6 was coupled with 3,4,5-trimethoxyphenyl acetylene, followed by mercury-catalyzed cyclization reaction afford compound 2 in 79% overall yield. Raloxifene (1) was prepared from compound 6 in four steps and 33% overall yield via coupling reaction with 1-trimethylsily-2-(4-tert-butyldimethylsiloxy)phenylethyne, mercury-catalyzed cyclization reaction, alkylation and demethylation.

A NEW SYNTHESIS OF 2-SUBSTITUTED BENZOFURANS AND BENZOTHIOPHENS: NOVEL FRAGMENTATION REACTIONS OF SIMPLE ALKYL GROUPS

Flash vacuum pyrolysis of (2-methoxy- and (2-methylthiobenzoyl)alkylidenetriphenylphosphoranes results in loss of Ph3PO and methyl radical; cyclisation of the resulting radical intermediates leads to benzofurans and benzothiophens in which the 2-substituents have undergone novel fragmentation processes.