75934-26-8

Upstream product

• 108-69-0 3,5-dimethylaminoaniline 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 108-38-3 m-xylene 
• 645-36-3 2,2-diethoxy-ethanamine 
• 325142-93-6 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 75934-34-8 N-(2,2-Diethoxy-ethyl)-N-(3,5-dimethyl-phenyl)-2,2,2-trifluoro-acetamide 
• 1429616-73-8 N-benzyl-N-(2,2-diethoxyethyl)-3,5-dimethylaniline 
• 1429616-77-2 1-benzyl-4,6-dimethyl-1H-indole 

Relevant academic research and scientific papers

Arenes to anilines and aryl ethers by sequential iridium-catalyzed borylation and copper-catalyzed coupling

(Chemical Equation Presented) N-Alkyl- and N-arylanilines were synthesized from arenes by a two-step sequence of iridium-catalyzed borylation and copper-catalyzed coupling with amines. Diaryl ethers were obtained by a related sequence of arene borylation, followed by coupling with phenols. In particular, 3,5-disubstituted arylamines and aryl ethers were prepared by initiating this sequence with meta-substituted arenes.

SYNTHESIS OF INDOLES FROM N-(TRIFLUOROACETYL)-2-ANILINO ACETALS

N-(trifluoroacetyl)indoles (3) are produced in high yield from appropriately ring-substituted N-(trifluoroacetyl)-2-anilino acetals (2) in boiling trifluoroacetic acid containing excess trifluoroacetic anhydride.Mild saponification provides the free indoles nearly quantitatively.The scope of the reaction is discussed.The ring closure follows solvolytic substitution of a trifluoroacetoxy group for one of the ethoxy groups in 2.The method has been extended to cyclization of N-(trifluoroacetyl)-α-anilinoacetone in hot polyphosphoric acid followed by saponification to yield 3-methylindole.