697-73-4Relevant articles and documents
Synthesis of mono- and difluorobenzyl chlorides by chlorination of mono- and difluorotoluenes with CCl4 and t-BuOCl induced by iron-containing catalysts
Bayguzina, Alfiya R.,Gallyamova, Leysan I.,Khalilov, Leonard M.,Khusnutdinov, Ravil I.
supporting information, (2019/07/19)
Mono- and difluorobenzyl chlorides were synthesized by chlorination of mono- and difluorotoluenes with CCl4?MeOH or t-BuOCl in the presence of iron-containing catalysts.
From alcohol to 1,2,3-triazole: Via a multi-step continuous-flow synthesis of a rufinamide precursor
Borukhova, Svetlana,No?l, Timothy,Metten, Bert,De Vos, Eric,Hessel, Volker
, p. 4947 - 4953 (2016/10/06)
Rufinamide is an antiepileptic drug used to treat the Lennox-Gastaut syndrome. It comprises a relatively simple molecular structure. Rufinamide can be synthesized from an organohalide in three steps. Recently we have shown that microreactor flow networks have better sustainability profiles in terms of life-cycle assessment than the respective consecutive processing in a batch. The analysis was based on the results of a single step conversion from batch to continuous mode. An uninterrupted continuous process towards rufinamide was developed, starting from an alcohol precursor, which is converted to the corresponding chloride with hydrogen chloride gas. The chloride is then converted to the corresponding organoazide that yields the rufinamide precursor via cycloaddition to the greenest and cheapest dipolarophile available on the market. The current process demonstrates chemical and process-design intensification aspects encompassed by novel process windows. Single reaction steps are chemically intensified via a wide range of conditions available in a microreactor environment. Meanwhile, the connection of reaction steps and separations results in process-design intensification. With two in-line separations the process consists of five stages resulting in a total yield of 82% and productivity of 9 g h-1 (11.5 mol h-1 L-1). The process minimizes the isolation and handling of strong alkylating or energetic intermediates, while minimizing water and organic solvent consumption.
Hydrogen Chloride Gas in Solvent-Free Continuous Conversion of Alcohols to Chlorides in Microflow
Borukhova, Svetlana,No?l, Timothy,Hessel, Volker
supporting information, p. 568 - 573 (2016/03/04)
Chlorides represent a class of valuable intermediates that are utilized in the preparation of bulk and fine chemicals. An earlier milestone to convert bulk alcohols to corresponding chlorides was reached when hydrochloric acid was used instead of toxic and wasteful chlorinating agents. This paper presents the development of an intensified solvent-free continuous process by using hydrogen chloride gas only. The handling of corrosive hydrogen chloride became effortless when the operating platform was split into dry and wet zones. The dry zone is used to deliver gas and prevent corrosion, while the wet zone is used to carry out the chemical transformation. The use of gas instead of hydrochloric acid allowed a decrease in hydrogen chloride equivalents from 3 to 1.2. In 20 min residence time, full conversion of benzyl alcohol yielded 96 wt % of benzyl chloride in the product stream. According to green chemistry and engineering principles, the developed process is of an exemplary type due to its truly continuous nature, no use of solvent and formation of water as a sole byproduct.
