857275-83-3

Upstream product

• 773837-37-9 sodium cyanide 
• 1261796-01-3 (2-methoxy-4-methylphenyl)methanol 
• 10542-80-0 (2-methoxy-4-methylphenyl)methanol 
• 81245-24-1 methyl 4-methyl-2-methoxybenzoate 
• 50-85-1 2-hydroxy-p-toluic acid 
• 122488-82-8 2-methoxy-4-methylbenzyl bromide 
• 7405-12-1 2-(hydroxymethyl)-5-methylphenol 

Downstream Products

• 1174551-02-0 2-(cyanomethyl)-5-methylphenyl benzoate 
• 1174551-15-5 2-amino-3-benzoyl-6-methylbenzo[b]furan 

Relevant academic research and scientific papers

Palladium-catalyzed three-component coupling reactions of 2-(cyanomethyl)phenol, aryl halides, and carbon monoxide

Three-component coupling reactions of 2-(cyanomethyl)phenol, aryl halides, and carbon monoxide (CO) in orthogonal-tandem catalysis were investigated. In the reactions, 2-(cyanomethyl)phenyl esters, which are produced through Pd(PPh3)4-catalyzed alkoxycarbonylation of aryl halides with 2-(cyanomethyl)phenol, undergo cycloisomerization in situ catalyzed by Pd(PCy3)2 as a co-catalyst to give 3-acyl-2-aminobenzofurans. Palladium species with homoleptic tertiary phosphines, such as Pd(PPh3)4 and Pd(PCy3)2, can catalyze the mechanistically distinct reactions in an orthogonal-tandem manner without interference. By switching the base used in this reaction, 3-acyl-2-(N-acylamino)benzofurans were obtained as major products instead of 3-acyl-2-aminobenzofurans. Given that 2-(cyanomethyl)phenols can be synthesized from commercially available salicylic acid derivatives in two steps, the present method thus provides facile access to synthetically useful 3-acyl-2-aminobenzofurans.

One-pot transition-metal-free synthesis of dibenzo[b,f]oxepins from 2-halobenzaldehydes

A one-pot transition-metal-free, base-mediated synthesis of dibenzo[b,f]oxepins was developed. The reaction of 2-halobenzaldehydes with (2-hydroxyphenyl)acetonitriles proceeds via a sequential aldol condensation and intramolecular ether formation reaction in the presence of Cs2CO 3 and molecular sieves in toluene.