Generation of 1,2-Difluorobenzene via a Photochemical Fluorodediazoniation Step in a Continuous Flow Mode

被引：11

作者：

Simon, Kevin ^{[1
,2
]}

Znidar, Desiree ^{[1
,2
]}

Boutet, Julien ^{[3
]}

Guillamot, Gerard ^{[3
]}

Lenoir, Jean-Yves ^{[3
]}

Dallinger, Doris ^{[1
,2
]}

Kappe, C. Oliver ^{[1
,2
]}

机构：

[1] Res Ctr Pharmaceut Engn GmbH RCPE, Ctr Continuous Flow Synth & Proc CCFLOW, A-8010 Graz, Austria

[2] Karl Franzens Univ Graz, Inst Chem, NAWI Graz, A-8010 Graz, Austria

[3] Seqens SAS, F-69130 Ecully, France

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2023年 / 27卷 / 02期

关键词：

Balz-Schiemann reaction; photochemistry; HF; pyridine; fluorination; continuous flow; BALZ-SCHIEMANN REACTION; AROMATIC FLUORIDES; FACILE PREPARATION; FLUORINATION; HYDROGEN; DEDIAZONIATION; DIAZOTIZATION; ANILINES;

D O I：

10.1021/acs.oprd.2c00348

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A proof-of-concept study for the synthesis of 1,2-difluorobenzene from 2-fluoroaniline via the Balz-Schiemann reaction using HF/pyridine as the fluorinating reagent is reported. Key to success for a fast reaction, a clean reaction profile-and thus high product selectivity-was a photochemically induced fluorodediazoniation of the in situ-generated diazonium salt performed in a continuous flow mode. A high-power 365 nm light-emitting diode provided a more robust and efficient irradiation system compared to a medium-pressure Hg lamp with respect to the reaction performance on scale-out runs and reaction time, allowing the generation of 1,2-difluorobenzene within a 10 min residence time and a product selectivity of >= 95% at full conversion.

引用

页码：322 / 330

页数：9

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