A Facile Method for Multigram Scale Light-Induced Synthesis of 4′-(Bromomethyl)-2-cyanobiphenyl

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2024-04-10 DOI:10.1021/acs.oprd.3c00443

Steffen G. Sveegaard*,

引用次数: 0

Abstract

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.

Abstract Image

查看原文本刊更多论文

光诱导合成 4′-（溴甲基）-2-氰基联苯的多克级简便方法

我们开发了一种合成 4′-（溴甲基）-2-氰基联苯的便捷绿色方法，利用可见光引发自由基链反应，并以 H2O2/HBr 系统作为溴源。对一系列溶剂进行了测试，最终制定了一个多克方案，产品收率为 71%，纯度为 97%，除简单过滤和洗涤外，无需其他纯化步骤。研究发现，碳酸二乙酯是一种高效的绿色溶剂，可替代四氯化碳和氯苯等传统溶剂，而同样被视为绿色溶剂的 2-丙醇则适用于纯化步骤中的沉淀和洗涤。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.90

自引率

14.70%

发文量

251

审稿时长

2 months

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.

文献相关原料

公司名称	产品信息	采购帮参考价格