Continuous flow Friedel-Crafts acetylation of phenols and electron-rich arenes and heteroarenes

被引:3
|
作者
Saint-Jacques, Kevin [1 ]
Charette, Andre B. [1 ]
机构
[1] Univ Montreal, Ctr Continuous Flow Synth, Dept Chem, FRQNT Ctr Green Chem & Catalysis, 1375 Ave Therese Lavoie Roux, Montreal, PQ H2V 0B3, Canada
基金
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词
Friedel-Crafts; Flavonoids; Acetophenones; Electrophilic aromatic substitution; Heteroarenes; Biomass derived solvent;
D O I
10.1007/s41981-023-00270-4
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An expedient and efficient synthesis of acetyl phloroglucinol from phloroglucinol under continuous flow is reported. This compound is an important building block to access numerous flavonoids. The reported acetylation reaction of phloroglucinol is more efficient than under batch conditions (residence time of 1 min in flow vs 10-15 h in batch; >= 98% yield in flow vs 65-86% yield in batch), and proceeds without any formation of the diacetylated product. The desired product was produced with a throughput of >= 98 g/h using a simple set-up. The conditions that highlight the use of ethyl acetate, a biomass-derived solvent and acetic anhydride or acetyl chloride were tested in the Friedel-Crafts acetylation of other electron-rich phenols and heterocycles.
引用
收藏
页码:193 / 199
页数:7
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