Name: a scalable balz-schiemann reaction protocol in a continuous flow reactor
Uploaded: 2023-02-10T12:55:00
Description: Watch this Scientific Journal Video about A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor at JoVE.com

感谢深圳市科技计划（批准号：KQTD20190929172447117）的支持。

注意：根据材料安全数据表（MSDS），仔细检查此处描述的化学品的特性和毒性，以便对相关材料进行适当的化学处理。使用的一些化学品对健康有害，必须特别小心。避免吸入和接触这些物质的皮肤。请全程穿戴合适的个人防护装备。
1. 连续流方案的进料准备
<ol><li>购买BF3·等2O，浓度为 8.1 mmol/mL。在玻璃瓶上贴上2.5公斤BF3·et2o...

<ol>
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F. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Handling+diazonium+salts+in+flow+for+organic+and+material+chemistry.">Handling diazonium salts in flow for organic and material chemistry.</a> Organic Chemistry Frontiers. 2 (5), 590-614 (2015).</li><li>Fortt, R., Wootton, R., Mello, A. D. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Continuous-flow+generation+of+anhydrous+diazonium+species:+Monolithic+microfluidic+reactors+for+the+chemistry+of+unstable+intermediates.">Continuous-flow generation of anhydrous diazonium species: Monolithic microfluidic reactors for the chemistry of unstable intermediates.</a> Organic Process Research &amp; Development. 7 (5), 762-768 (2003).</li><li>Liu, Y., Zeng, C., Wang, C., Zhang, L. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Continuous+diazotization+of+aromatic+amines+with+high+acid+and+sodium+nitrite+concentrations+in+microreactors.">Continuous diazotization of aromatic amines with high acid and sodium nitrite concentrations in microreactors.</a> Journal of Flow Chemistry. 8 (3-4), 139-146 (2018).</li><li>Arlene, B., Aisling, L., Alex, C. P., Marcus, B. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Forgotten+and+forbidden+chemical+reactions+revitalised+through+continuous+flow+technology.">Forgotten and forbidden chemical reactions revitalised through continuous flow technology.</a> Organic &amp; Biomolecular Chemistry. 19 (36), 7737-7753 (2021).</li><li>Jianli, C., Xiaoxuan, X., Jiming, L., Zhiqun, Y., Weike, S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Revisiting+aromatic+diazotization+and+aryl+diazonium+salts+in+continuous+flow:+highlighted+research+during+2001-2021.">Revisiting aromatic diazotization and aryl diazonium salts in continuous flow: highlighted research during 2001-2021.</a> Reaction Chemistry &amp; Engineering. 7 (6), 1247-1275 (2022).</li><li>Li, B., Widlicka, D., Boucher, S., Hayward, C., Young, J. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Telescoped+flow+process+for+the+syntheses+of+N-Aryl+pyrazoles.">Telescoped flow process for the syntheses of N-Aryl pyrazoles.</a> Organic Process Research &amp; Development. 16 (12), 2031-2035 (2012).</li><li>Zhi, Y., Yan, L., Chuan, Y., Wei-ke, S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Continuous+flow+reactor+for+Balz-Schiemann+reaction:+a+new+procedure+for+the+preparation+of+aromatic+fluorides.">Continuous flow reactor for Balz-Schiemann reaction: a new procedure for the preparation of aromatic fluorides.</a> Tetrahedron Letters. 54 (10), 1261-1263 (2013).</li><li>Li, B., Steven, G. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Development+of+flow+processes+for+the+syntheses+of+N-aryl+pyrazoles+and+diethyl+cyclopropane-cis-1,2-dicarboxylate.">Development of flow processes for the syntheses of N-aryl pyrazoles and diethyl cyclopropane-cis-1,2-dicarboxylate.</a> Acs Symposium. 1181 (14), 383-402 (2014).</li><li>Zhiqun, Y., Hei, D., Xiaoxuan, X., Jiming, L., Weike, S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Continuous-Flow+diazotization+for+efficient+synthesis+of+Methyl+2-(Chlorosulfonyl)benzoate:+An+example+of+inhibiting+parallel+side+reactions.">Continuous-Flow diazotization for efficient synthesis of Methyl 2-(Chlorosulfonyl)benzoate: An example of inhibiting parallel side reactions.</a> Organic Process Research &amp; Development. 20 (12), 2116-2123 (2016).</li><li>Jiming, L., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Continuous-flow+double+diazotization+for+the+synthesis+of+m-difluorobenzene+via+Balz-Schiemann+reaction.">Continuous-flow double diazotization for the synthesis of m-difluorobenzene via Balz-Schiemann reaction.</a> Journal of Flow Chemistry. 10 (4), 589-596 (2020).</li><li>Zhiqun, Y., Yanwen, L., Chuanming, Y. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=A+Continuous+kilogram-scale+process+for+the+manufacture+of+o-Difluorobenzene.">A Continuous kilogram-scale process for the manufacture of o-Difluorobenzene.</a> Organic Process Research &amp; Development. 16 (10), 1669-1672 (2012).</li><li>Hathaniel, H. P., Timothyl, J. S., Stephen, L. B. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Rapid+synthesis+of+aryl+fluorides+in+continuous+flow+through+the+Balz-Schiemann+reaction.">Rapid synthesis of aryl fluorides in continuous flow through the Balz-Schiemann reaction.</a> Angewandte Chemie International Edition. 55 (39), 11907-11911 (2016).</li><li>David, R. S., Fran&#231;ois, L., William, J. M., John, R. N. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=An+improved+Balz-Schiemann+reaction+enabled+by+ionic+liquids+and+continuous+processing.">An improved Balz-Schiemann reaction enabled by ionic liquids and continuous processing.</a> Tetrahedron. 75 (32), 4261-4265 (2019).</li><li>He, G., Wang, D., Liang, C., Chen, H. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Theoretical+study+on+thermal+safety+of+preparing+fluorobenzene+by+the+Balz-Schiemann+reaction+and+fluorodenitration+reaction.">Theoretical study on thermal safety of preparing fluorobenzene by the Balz-Schiemann reaction and fluorodenitration reaction.</a> Journal of Chemical Health &amp; Safety. 20 (1), 30-34 (2013).</li><li>Schotten, C., Leprevost, S. K., Yong, L. M., Hughes, C. E., Browne, D. 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Balz-Schiemann反应的连续流动方案已经通过微通道流动反应器和动态混合流动反应器的组合成功执行。与间歇工艺相比，该策略具有以下几个优点：（i）受控重氮盐形成更安全;（ii）它更适合更高的反应温度，10°C与-20°C;（iii）无需隔离重氮中间体即可提高效率，在一个连续过程中分为两步。具体来说，连续流动设备设置过程对于该协议至关重要，因为除了化学转化之外，流动过程的可靠性主要取?...

Balz−Schiemann反应是一种经典的方法，通过在不使用溶剂1，2的情况下加热ArN2 + BF4−来用氟取代重氮基团。该反应可应用于多种芳基胺底物，使其成为合成芳基胺的普遍适用方法，芳基胺经常用于制药或精细化工行业的高级中间体2，3。不幸的是，巴尔茨-席曼反应中经常采用苛刻的反应条件，并且反应生成具有潜在爆炸性的芳基重氮盐4，5，6，7，8。与Balz-Schiemann反应相关的其他挑战是在热分解过程中形成副产物及其适度的产率。为了尽量减少副产物的形成，可以在非极性溶剂中或使用纯重氮盐9，10进行热脱氮，这意味着芳基二氮盐应被分离。然而，芳香胺的重氮化通常是放热和快速的，这是与分离爆炸性重氮盐相关的风险，特别是在大规模生产中。
近年来，连续流动合成技术有助于克服与Balz-Schiemann反应相关的安全问题11，12。尽管有一些使用连续微反应器在对芳基氯、5-偶氮和氯磺酰化的位置进行脱氨的芳胺重氮化的例子，但这些贡献仅在实验室规模上报告13，14，15，16，17。Yu及其同事开发了一种连续的千克级工艺，用于合成芳基氟化物18。他们已经表明，改善流动系统的传热和传质将有利于重氮化过程和氟化过程。然而，他们使用了两个独立的连续流反应器;因此，分别研究了重氮化和热分解过程。Buchwald及其同事19发表了进一步的贡献，他们提出了一个假设，即如果产物形成通过SN2Ar或SN1机制进行，那么可以通过增加氟化物源的浓度来提高产量。他们开发了一种流动到连续搅拌釜式反应器（CSTR）混合工艺，其中重氮盐以连续和受控的方式产生和消耗。然而，作为管流反应器，连续搅拌罐式反应器的传热和传质效率还不够好，不能指望大型连续搅拌罐式连续搅拌罐与爆炸性重氮盐一起大规模生产。随后，Naber及其同事开发了一种完全连续的流动工艺，从2，6-二氨基嘌呤20合成2-氟腺嘌呤。他们发现放热Balz-Schiemann反应在连续流动方式下更容易控制，并且流动反应器的管道尺寸会影响传热和温度控制方面 - 大尺寸的管式反应器显示出积极的改进。然而，管式反应器的放大效应会显著，极性芳基重氮盐在有机溶剂中的溶解度差，给面临堵塞风险的静态管式反应器带来麻烦。尽管已经取得了显著进展，但大规模巴尔茨-席曼反应仍然存在一些问题。因此，开发一种改进的方案，以提供对芳基氟的快速和可扩展的获取仍然具有重要意义。
与大规模Balz-Schiemann反应处理相关的挑战包括：（i）在短时间内积累的重氮中间体的热不稳定性21;（ii） 处理时间长;（iii）重氮氟硼酸盐中加热不均匀或存在水，导致无法控制的热分解和副产物形成增加22，23。此外（iv）在某些流动处理模式下，由于其低溶解度14，仍然需要分离重氮中间体，然后将其送入不受控制的速率分解反应中。处理大量在线重氮盐的风险是无法避免的。因此，开发连续流动策略以解决上述问题并避免不稳定重氮物种的积累和分离具有显着的好处。
为了在药品中建立本质上更安全的化学品生产，我们集团专注于多步连续流动技术。在这项工作中，我们将这项技术应用于千克级的Balz-Schiemann合成，以消除芳基重氮盐的分离，同时促进有效的氟化。

<table border="1" fo:keep-together.within-page="1" fo:keep-with-next.within-page="always">
	<tbody>
		<tr>
			<td>2-Methylpyridin-3-amine</td>
			<td>Raffles Pharmatech Co. Ltd</td>
			<td>C2021236-SM5-H221538-008</td>
			<td>HPLC: &#62;98%, Water by KF &#8804;0.5%</td>
		</tr>
		<tr>
			<td>316L piston constant flow pump</td>
			<td>Oushisheng (Beijing) Technology Co.,Ltd</td>
			<td>DP-S200</td>
			<td></td>
		</tr>
		<tr>
			<td>BF3.Et2O</td>
			<td>Whmall.com</td>
			<td>B802217</td>
			<td></td>
		</tr>
		<tr>
			<td>Citric acid</td>
			<td>Titan Technology Co., Ltd</td>
			<td>G83162G</td>
			<td></td>
		</tr>
		<tr>
			<td>con.HCl</td>
			<td>Foshang Xilong Huagong</td>
			<td>1270110101601M&#160;&#160;</td>
			<td></td>
		</tr>
		<tr>
			<td>Dynamically mixed flow reactor</td>
			<td>Autichem Ltd</td>
			<td>DM500</td>
			<td>316L reator with 500 mL of internal volume</td>
		</tr>
		<tr>
			<td>Heptane</td>
			<td>Shenzhen Huachang</td>
			<td>HCH606</td>
			<td>Water by KF &#8804;0.5%</td>
		</tr>
		<tr>
			<td>Micro flow reactor</td>
			<td>Corning Reactor Technology Co.,Ltd</td>
			<td>G1 Galss AFR</td>
			<td>Glass module with 9 mL of internal volume</td>
		</tr>
		<tr>
			<td>PTFE piston constant flow pump</td>
			<td>Sanotac China</td>
			<td>MPF1002C</td>
			<td></td>
		</tr>
		<tr>
			<td>Sodium hydroxide</td>
			<td>Foshang Xilong Huagong</td>
			<td>1010310101700</td>
			<td></td>
		</tr>
		<tr>
			<td>tert-Butyl methyl ether</td>
			<td>Titan Technology Co., Ltd</td>
			<td>01153694</td>
			<td></td>
		</tr>
		<tr>
			<td>tert-Butyl nitrite</td>
			<td>Whmall.com</td>
			<td>XS22030900060</td>
			<td></td>
		</tr>
		<tr>
			<td>Tetrahydrofuran</td>
			<td>Titan Technology Co., Ltd</td>
			<td>1152930</td>
			<td>Water by KF &#8804;0.5%</td>
		</tr>
	</tbody>
</table>

a scalable balz-schiemann reaction protocol in a continuous flow reactor

制药和精细化工行业对芳烃氟化物的需求正在稳步增长。Balz-Schiemann反应是通过制备和转化重氮四氟硼酸盐中间体 ，从 芳基胺制备芳基氟化物的直接策略。然而，在扩大规模时处理芳基重氮盐存在重大安全风险。为了尽量减少危害，我们提出了一种连续流动方案，该方案已在千克尺度上成功执行，该协议消除了芳基重氮盐的分离，同时促进了有效的氟化。重氮化过程在10 °C下进行，停留时间为10 min，然后在60 °C下进行氟化过程，停留时间为5.4 s，收率约为70%。通过引入这种多步连续流动系统，反应时间已大大缩短。

模型反应如图2所示。选择2-甲基吡啶-3-胺（图2中的化合物1）作为起始原料，通过Balz-Schiemann反应制备2-甲基吡啶-3-氟化物（图2中的化合物3）。通过改变反应温度和停留时间对实验参数进行了系统研究。饲料A是0.35M 2-甲基吡啶-3-胺的THF溶液。饲料B是纯BF3·等2O，浓度为8.1M。进料A和进料B首先被引入预混合和?...

Watch this Scientific Journal Video about A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor at JoVE.com

A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor

提出了一个详细的可扩展连续流动方案，用于通过Balz-Schiemann反应从芳基胺合成芳基氟化物。

连续流反应器中的可扩展巴尔茨-席曼反应方案

The demand for aromatic fluorides is steadily increasing in the pharmaceutical and fine chemical industries. The Balz-Schiemann reaction is a ...

我们的方案是一种以连续流动方式从芳基胺制备芳基氟化物的简单策略。安全、可控、高效。这项措施可以提供对精细化工和制药行业的洞察，从而形成安全可靠的过程。请小心并专心执行此技术。首先，在尝试此技术之前，请阅读所有步骤并找出操作细节。为了在连续流系统中进行Balz-Schiemann反应，请准备两个内部反应体积为9毫升的微流反应器模块和一个内部反应体积为500毫升的动态混合管式反应器。此外，准备一个带 PTFE 泵头的恒流泵和三个带 316 L 不锈钢泵头的恒流泵。按照手稿中的描述组装设备。使用前检查泵、管道和流动反应器之间所有连接的机械完整性。设置泵的流量。然后将夹套出口、预混和重氮盐形成区的温度设置为零下5摄氏度，热分解区的夹套出口温度设置为60摄氏度，以保持温度调节。要检查设备安全性和泄漏，首先将泵 A、B、C 和 D 的计量管道放入进料 E 瓶中。并将管道排放到垃圾收集瓶中。然后启动泵并缓慢调节背压至三巴。观察每个泵的稳定性，并检查所有接头、管道和反应器是否有任何溶剂泄漏。此外，检查每个区域的夹套入口和出口温度以及每个泵的当前入口压力是否在目标范围内。然后，在稳态平衡 10 分钟后停止泵。要开始反应过程，将加药管道的A，B，C和D放入相应的进料中，然后将出料管道放入废物收集瓶中。同时启动泵A和B并记录时间。然后在 30 秒后启动泵 C，在 8 分钟后启动泵 D。稳态平衡10分钟后，将卸料管线放入产品收集容器中。观察并记录每个区域的温度和每个泵的压力。进料 B 泵送完成后，将加药管道 B 插入进料 E，然后将出料管道放入废物收集瓶中。并将加药管道的A、C和D放入进料E瓶中。清洗 10 分钟后关闭泵 A、B、C 和 D。连续流反应器成功地应用于模型衬底上的巴尔茨-席曼反应。流动实验的反应温度成功控制在10摄氏度，粗品纯度为70%，高于批量处理得到的温度。几乎 98% 的转换是在居民时间的 600 秒内达到的。当重氮化区的流速为每分钟50毫升，热分解区的流速为5.4秒时，流速为每分钟100毫升。增加流速会在反应中留下大量的起始材料，降低流速可能会完全消耗起始材料，但会限制生产效率。粗产物使用质谱、质子-核磁共振和氟-核磁共振进一步纯化和分析。重要的是要根据物质的化学性质和吸收性证明反应器是泵，特别是对于那些高度或那些与固体形成的反应。具有液体效应和更快反应速率的反应可以使用连续流动系统进行有效。此外，它会引起反应，可能会或可能不会导致固体的形成。

Research

JoVE Journal

Chemistry

Preparation and Use of Samarium Diiodide (SmI2) in Organic Synthesis: The Mechanistic Role of HMPA and Ni(II) Salts in the Samarium Barbier Reaction

Preparation and Use of Samarium Diiodide SmI2 in Organic Synthesis: The Mechanistic Role of HMPA and NiII Salts in the Samarium Barbier Reaction

二碘化钐的制备和使用（SMI<sub&gt; 2</sub&gt;）在有机合成中：HMPA和镍（II）盐的钐巴尔比耶反应的机理作用

Although initially considered an esoteric reagent, SmI2 has become a common tool for synthetic organic chemists. SmI2 is generated through the addition of ...

科研

化学

Untargeted Metabolomics from Biological Sources Using Ultraperformance Liquid Chromatography-High Resolution Mass Spectrometry (UPLC-HRMS)

Untargeted Metabolomics from Biological Sources Using Ultraperformance Liquid Chromatography-High Resolution Mass Spectrometry UPLC-HRMS

不相关的代谢组学，生物源使用超高效液相色谱 - 高分辨质谱（UPLC-HRMS）

Here we present a workflow to analyze the metabolic profiles for biological samples of interest including; cells, serum, or tissue. The sample is first ...

A Simple and Rapid Protocol for Measuring Neutral Lipids in Algal Cells Using Fluorescence

一种简单快速的协议用荧光测量中性脂肪在藻细胞

Algae are considered excellent candidates for renewable fuel sources due to their natural lipid storage capabilities. Robust monitoring of algal ...

Real-time Monitoring of Reactions Performed Using Continuous-flow Processing: The Preparation of 3-Acetylcoumarin as an Example

反应执行使用连续流处理的实时监控：3  - 乙酰基香豆素的制备为例

By using inline monitoring, it is possible to optimize reactions performed using continuous-flow processing in a simple and rapid way. It is also possible ...

Post Column Derivatization Using Reaction Flow High Performance Liquid Chromatography Columns

柱后衍生用反应流高效液相色谱柱

A protocol for the use of reaction flow high performance liquid chromatography columns for methods employing post column derivatization (PCD) is ...

Synthesis and Exfoliation of Discotic Zirconium Phosphates to Obtain Colloidal Liquid Crystals

合成与盘状磷酸盐锆剥落获取胶体液晶

Due to their abundance in natural clay and potential applications in advanced materials, discotic nanoparticles are of interest to scientists and ...

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

使用有机锂试剂的一个协议安全的锂化反应

Organolithium reagents are powerful tools in the synthetic chemist&#39;s toolbox. However, the extreme pyrophoric nature of the most reactive reagents ...

A Protocol for Electrochemical Evaluations and State of Charge Diagnostics of a Symmetric Organic Redox Flow Battery

- 电化学评估和对称有机氧化还原液流电池的充电诊断状态协议

Redox flow batteries have been considered as one of the most promising stationary energy storage solutions for improving the reliability of the power grid ...

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

连续流动化学: Diphenyldiazomethane 与p硝基苯甲酸的反应

Continuous flow technology has been identified as instrumental for its environmental and economic advantages leveraging superior mixing, heat transfer and ...

Combustion Chemistry of Fuels: Quantitative Speciation Data Obtained from an Atmospheric High-temperature Flow Reactor with Coupled Molecular-beam Mass Spectrometer

燃料燃烧化学: 用耦合分子束质谱仪从大气高温流反应器中获得的定量形态数据

This manuscript describes a high-temperature flow reactor experiment coupled to the powerful molecular beam mass spectrometry (MBMS) technique. This ...