A convenient method for the preparation of mono- and bis-substituted photochromic bis(benzothienyl)perfluorocyclopentenes via regioselective Friedel–Crafts acylation

Bogacheva, Anna M.; Yarovenko, V. N.; Levchenko, K. S.; Кобелева, О. И.; Валова, Т. М.; Barachevsky, V. А.; Стручкова, Марина И.; Shmelin, P. S.; Krayushkin, M. M.; Charushin, Valery N.

doi:10.1016/j.tetlet.2012.08.111

Cited by 9 publications

(1 citation statement)

References 14 publications

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“…SM01, SM02-imA, SM01-imA, and LM49-01-imA were not detected in the LM49-01 test sample, but an unknown single impurity LM49-01-imX was identified with its content below 0.05%. In addition, the system of methylene chloride and AlCl 3 commonly used in Friedel-Crafts acylation was employed in this experiment [15,16]. In consideration of the possibility of chloromethylation, we carefully analyzed the MS and HPLC data of LM49-01 test sample.…”

Section: Process Verification Of Friedel-crafts Acylation Stepmentioning

confidence: 99%

Process Development and Synthesis of Process-Related Impurities of an Efficient Scale-Up Preparation of 5,2′-Dibromo-2,4′,5′-Trihydroxy Diphenylmethanone as a New Acute Pyelonephritis Candidate Drug

Feng

Cui

et al. 2020

Molecules

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Based on a foregoing gram-scale laboratory process, an efficient scale-up preparation process of 5,2′-dibromo-2,4′,5′-trihydroxydiphenylmethanone (LM49-API), a new acute pyelonephritis candidate drug, was developed and validated aiming to reduce by-products and achieve better impurity profiles. Meanwhile, the polymorph of LM49-API and process-related impurities were also investigated. Ultimately, the optimal reaction conditions were verified by evaluating the impurity profiles and their formation during the synthesis. Six process-related impurities were synthesized and identified, being useful for the quality control of LM49-API. Its finalized preparation process was further validated at 329–410 g scale-up production in 53.4–57.1% overall yield with 99.95–99.98% high-performance liquid chromatography (HPLC) purity, and it is currently viable for commercial production. LM49-API-imC and LM49-API-imX were identified as the main single impurities in LM49-API, with the content controlled to be less than 0.03%.

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Section: Process Verification Of Friedel-crafts Acylation Stepmentioning

confidence: 99%