《Systematic Investigation into the Formation of Significant Amounts of Unknown Impurity during Scale-up of NaBH4-I2 Mediated Reduction of Nitro-Amide Intermediate of Mirabegron》 was written by Deshmukh, Dattatray G.; Bangal, Mukund N.; Kalawade, Kaustubh A.; Mathad, Vijayavitthal T.. Synthetic Route of C6H11BrO2 And the article was included in Organic Process Research & Development in 2020. The article conveys some information:
After successful development of a manufacturing process for the Mirabegron (I) at the laboratory scale, a muddled situation was aroused during the scale-up batches, wherein sodium borohydride-iodine (NaBH4-I2) mediated reduction of nitro-amide II ended up with substantial amounts (∼10%) of unspecified impurity in the nitro-amine intermediate III. On the basis of the structure elucidation and meticulous investigation, a reaction path for its genesis during the process was identified and an efficient mechanism proposed to arrest its formation. In-situ generated nickel boride (Ni2B) due to reaction of NiI2 (corrosion product) with NaBH4 followed by electrophilic attack of THF (solvent) was found to be the reason for the formation of impurity (IV). Execution of subsequent batches with proper controls arrested this impurity and successfully provided the Mirabegron with the desired quality. In the experiment, the researchers used Ethyl 4-bromobutyrate(cas: 2969-81-5Synthetic Route of C6H11BrO2)
Ethyl 4-bromobutyrate(cas: 2969-81-5) belongs to bromides. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact.Synthetic Route of C6H11BrO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary