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General Description

4-(2-bromo-3-methoxyphenyl)morpholine is an organic compound that belongs to the class of morpholine derivatives. It is also known as 2-Bromo-3-methoxy-4-morpholinoaniline. This chemical consists of a morpholine ring attached to a phenyl group that has a bromo and methoxy substituent. 4-(2-bromo-3-methoxyphenyl)morpholine has potential applications in the field of pharmaceuticals and agrochemicals due to its morpholine and phenyl moieties which are known to exhibit biological activities. However, further research and testing are needed to fully understand its potential uses and effects.

Upstream product

• 578-57-4 2-bromoanisole 
• 98022-77-6 N-bromomorpholine 
• 217813-03-1 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate 

Relevant academic research and scientific papers

Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis

Palladium/norbornene (Pd/NBE) cooperative catalysis has emerged as a useful tool for preparing poly substituted arenes; however, its substrate scope has been largely restricted to aryl iodides. While aryl bromides are considered as standard substrates for Pd-catalyzed cross coupling reactions, their use in Pd/NBE catalysis remains elusive. Here we describe the development of general approaches for aryl bromide-mediated Pd/NBE cooperative catalysis. Through careful tuning the phosphine ligands and quenching nucleophiles, ortho amination, acylation and alkylation of aryl bromides have been realized in good efficiency. Importantly, various heteroarene substrates also work well and a wide range of functional groups are tolerated. In addition, the utility of these methods has been demonstrated in sequential cross coupling/ortho functionalization reactions, consecutive Pd/NBE-catalyzed difunctionalization to construct penta-substituted aromatics and two-step meta functionalization reactions. Moreover, the origin of the ligand effect in ortho amination reactions has been explored through DFT studies. It is expected that this effort would significantly expand the reaction scope and enhance the synthetic potential for Pd/NBE catalysis in preparing complex aromatic compounds.

Synthesis of ortho -haloaminoarenes by aryne insertion of nitrogen-halide Bonds

A rapid and general access to ortho-haloaminoarenes has been developed by aryne insertion into N-chloramine, N-bromoamine, and N-iodoamine bonds via two complementary protocols harnessing fluoride-promoted 1,2-elimination of ortho-trimethylsilyl aryltriflates. Typically, electron-deficient N-chloramines effectively react with aryne intermediates generated at elevated temperature with CsF, while less stable N-haloamines are found more efficient under milder, TBAF-mediated aryne formation at room temperature. Both protocols demonstrate a good level of regioselectivity and functional group tolerance. Efforts to elucidate the mechanism of N-X insertion are also discussed. The practical value of this transformation is highlighted by rapid synthesis of novel analogues of the antipsychotic cariprazine.