Continuous-Flow Photobromination/Debromination Cascade for Synthesis of the Trifloxystrobin Intermediate
Bromination reactions involving bromine monomers tend to be polybrominated, resulting in poor product selectivity and subsequent separation difficulties. This proposal outlines a multistep cascade for continuous flow synthesis involving photobromination and debromination. The process comprises five...
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Veröffentlicht in: | Industrial & engineering chemistry research 2024-10, Vol.63 (42), p.17734-17743 |
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Sprache: | eng |
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Zusammenfassung: | Bromination reactions involving bromine monomers tend to be polybrominated, resulting in poor product selectivity and subsequent separation difficulties. This proposal outlines a multistep cascade for continuous flow synthesis involving photobromination and debromination. The process comprises five units: bromine generation, photobromination, quenching, water/oil separation, and photodebromination. A full-process continuous and efficient synthesis of the trifluorostrolibin intermediate (E)-Methyl-2-(2-broMoMethylphenyl)-2-MethoxyiMinoacetate (MBPA) was achieved. This process converts the byproduct (E)-Methyl-2-(2-dibroMoMethylphenyl)-2-MethoxyiMinoacetate into the target product MBPA. At a total residence time of 12.9 min, the conversion of (E)-Methy-2-(methoxyimino)-2-(o-toly) acetate reached 99.0%, and the total yield of MBPA reached 94.2%. Machine learning and quantum chemical calculations enhance the comprehension of photodebromination mechanisms. Simultaneously, through comprehensive simulations involving sensitivity and scenario analyses, the optimization of photon utilization emerged as a pivotal factor for improving the overall applicability of the production process. This method of synthesizing halogenated products is anticipated to play a crucial role in pharmaceuticals or pesticides. |
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ISSN: | 0888-5885 1520-5045 |
DOI: | 10.1021/acs.iecr.4c02202 |