Continuous Flow Synthesis of Substituted 3,4-Propylenedioxythiophene Derivatives,Organic Process Research & Development

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Continuous Flow Synthesis of Substituted 3,4-Propylenedioxythiophene Derivatives
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-01-31 , DOI: 10.1021/acs.oprd.2c00356
Dattatray L. Tarange ₁ , Nagaraj Nayak ₁ , Anil Kumar ₁

Affiliation

We report a continuous flow method for the process intensification of commercially important propylenedioxythiophene (ProDOT) monomers. A new four-step synthetic route was designed to make the whole process more economical and continuous flow amenable. Apart from being safe and having a higher throughput via continuous flow, we could optimize each of the synthetic steps to quantitative conversion. GC–MS analysis was used to monitor each of the processes during optimization. The overall process could be completed in around 65 min, starting from the commercially available materials, as compared to the few days via the reported batch processes. Furthermore, we have shown that the most critical step of the Williamson etherification could be intensified via continuous flow to the space–time yield (STY) of 63 g/h/L as compared to 0.16 g/h/L via the traditional batch process. As all the synthetic steps in our continuous flow process were optimized to quantitative conversions, it opens up the possibility of telescoping of the whole process. We believe that our findings will be able to fill the existing gap in the process intensification for the synthesis of commercially important ProDOT-based monomers.

中文翻译：

取代 3,4-丙烯二氧噻吩衍生物的连续流动合成

我们报告了一种用于商业上重要的丙烯二氧噻吩 (ProDOT) 单体工艺强化的连续流动方法。设计了一条新的四步合成路线，使整个过程更加经济和连续流。除了安全和通过连续流动具有更高的吞吐量之外，我们还可以优化每个合成步骤以进行定量转化。GC-MS 分析用于监测优化过程中的每个过程。从市售材料开始，整个过程可以在大约 65 分钟内完成，而通过报告的批处理过程则需要几天时间。此外，我们已经表明，与 0 相比，威廉姆森醚化最关键的步骤可以通过连续流动强化到 63 g/h/L 的时空产率 (STY)。16 g/h/L 通过传统的批处理。由于我们连续流动过程中的所有合成步骤都针对定量转换进行了优化，因此它开辟了整个过程可伸缩的可能性。我们相信，我们的研究结果将能够填补在商业上重要的基于 ProDOT 的单体合成过程强化方面的现有空白。

更新日期：2023-01-31

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