{"title":"光诱导合成 4′-（溴甲基）-2-氰基联苯的多克级简便方法","authors":"Steffen G. Sveegaard*, ","doi":"10.1021/acs.oprd.3c00443","DOIUrl":null,"url":null,"abstract":"<p >A convenient, green method to synthesize 4′-(bromomethyl)-2-cyanobiphenyl was developed, where visible light is used to initiate the radical chain reaction and the H<sub>2</sub>O<sub>2</sub>/HBr system as the bromine source. A range of solvents was tested, and a final multigram protocol was developed to give a good yield of 71% of product with 97% purity and no other purification than simple filtration and wash. Diethyl carbonate was found to be an efficient greener solvent alternative to classical solvents such as carbon tetrachloride and chlorobenzene, and 2-propanol, also considered a green solvent, was suitable for precipitation and washing in the purification step.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.1000,"publicationDate":"2024-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A Facile Method for Multigram Scale Light-Induced Synthesis of 4′-(Bromomethyl)-2-cyanobiphenyl\",\"authors\":\"Steffen G. Sveegaard*, \",\"doi\":\"10.1021/acs.oprd.3c00443\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A convenient, green method to synthesize 4′-(bromomethyl)-2-cyanobiphenyl was developed, where visible light is used to initiate the radical chain reaction and the H<sub>2</sub>O<sub>2</sub>/HBr system as the bromine source. A range of solvents was tested, and a final multigram protocol was developed to give a good yield of 71% of product with 97% purity and no other purification than simple filtration and wash. Diethyl carbonate was found to be an efficient greener solvent alternative to classical solvents such as carbon tetrachloride and chlorobenzene, and 2-propanol, also considered a green solvent, was suitable for precipitation and washing in the purification step.</p>\",\"PeriodicalId\":55,\"journal\":{\"name\":\"Organic Process Research & Development\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.1000,\"publicationDate\":\"2024-04-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Process Research & Development\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.oprd.3c00443\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Process Research & Development","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.oprd.3c00443","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
A Facile Method for Multigram Scale Light-Induced Synthesis of 4′-(Bromomethyl)-2-cyanobiphenyl
A convenient, green method to synthesize 4′-(bromomethyl)-2-cyanobiphenyl was developed, where visible light is used to initiate the radical chain reaction and the H2O2/HBr system as the bromine source. A range of solvents was tested, and a final multigram protocol was developed to give a good yield of 71% of product with 97% purity and no other purification than simple filtration and wash. Diethyl carbonate was found to be an efficient greener solvent alternative to classical solvents such as carbon tetrachloride and chlorobenzene, and 2-propanol, also considered a green solvent, was suitable for precipitation and washing in the purification step.
期刊介绍：
The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.
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