13397-96-1

Upstream product

• 778-28-9 butyl para-toluenesulfonate 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 122-56-5 tributyl borane 
• 54031-00-4 1-bromo-2-((trimethylstannyl)methyl)benzene 
• 1529-47-1 chlorotrimethylgermane 
• 109-72-8 n-butyllithium 
• 16692-57-2 1-bromo-2-(pent-1-en-1-yl)benzene 
• 158918-49-1 N’-(2-bromobenzylidene)-4-methylbenzenesulfonohydrazide 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 1438826-28-8 C₂₂H₃₉BO₃Si 
• 1438824-72-6 2-pentylphenyl dimethylsilane 
• 119150-38-8 <2-n-Amyl-benzhydryl>-<2-dimethylamino-aethyl>-aether 
• 101787-36-4 2-n-Amyl-benzhydrol 

Relevant academic research and scientific papers

Multiple organolithium generation in the continuous flow synthesis of amitriptyline

A continuous flow protocol for the preparation of the tricyclic antidepressant (TCA) amitriptyline is reported. The advantages of flow chemistry when handling organometallic agents as well as when performing reaction with gases are demonstrated. Continuous multilithiation combined with carboxylation and the Parham cyclization, a Grignard addition and thermolytic water elimination by inductive heating are key features of the multistep protocol. Copyright

A Facile Alkylation of Aryl Aldehyde Tosylhydrazone with Trialkylboranes

Trialkylboranes readily alkylate aryl aldehyde tosylhydrazones to produce either the corresponding arylalkane or aryl alcohol in excellent yields.

Iridium-catalyzed borylation of secondary benzylic C-H bonds directed by a hydrosilane

Most functionalizations of C-H bonds by main-group reagents occur at aryl or methyl groups. We describe a highly regioselective borylation of secondary benzylic C-H bonds catalyzed by an iridium precursor and 3,4,7,8-tetramethyl-1, 10-phenanthroline as the ligand. The reaction is directed to the benzylic position by a hydrosilyl substituent. This hydrosilyl directing group is readily deprotected or transformed to other functional groups after the borylation reaction, providing access to a diverse set of secondary benzylboronate esters by C-H borylation chemistry.

Alkylation of Aldehyde (Arenesulfonyl)hydrazones with Trialkylboranes

(Arenesulfonyl)hydrazone derivatives of aryl aldehydes are readily alkylated by trialkylboranes in the presence of base to generate new organoboranes that may be converted to the corresponding substituted alkanes or alcohols depending upon the reaction conditions chosen. Both tosyl- and trisylhydrazone derivatives can be utilized in the reaction, which tolerates a variety of functional groups, making it a versatile alternative to both the Grignard and Suzuki-coupling reactions.

Selective lithiation of 1-bromo-2-((trimethylstannyl)methyl)benzene: Synthesis of 1-bromo-2-(lithiomethyl)benzene, 1-lithio-2-((trimethylstannyl)methyl)benzene, and α,2-dilithiotoluene

Reactions of 1-bromo-2-((trimethylstannyl)methyl)benzene (1) with n-butyllithium and tert-butyllithium have been investigated. With n-butyllithium in tetrahydrofuran (THF) at -70°C, the only observed process was lithium-tin exchange, yielding 1-bromo-2-(lithiomethyl)benzene (2). In contrast, lithium-halogen exchange occurred when 1 was treated with tert-butyllithium in diethyl ether at -80°C to give 1-lithio-2-((trimethylstannyl)methyl)benzene (3). α,2-Dilithiotoluene could be prepared in high yield from 3 and tert-butyllithium in either diethyl ether (room temperature) or THF (-80°C).