Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 24, Issue 10, Pages 2208-2216Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.0c00239
Keywords
flow photochemistry; scale-up; bromine generator; photochemical halogenation; radical chemistry
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Funding
- Austrian COMET Program by the Austrian Federal Ministry of Transport, Innovation and Technology (BMVIT) [862766]
- Austrian Federal Ministry for Digital and Economic Affairs (BMDW) [862766]
- State of Styria (Styrian Funding Agency SFG) [862766]
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Although continuous flow technology can facilitate the scale-up of photochemical processes it is not yet routinely implemented on production scale in the fine chemical industries. This can be attributed to additional challenges compared to thermal processes, mostly in the homogeneous irradiation of the flow reactor. Here, we detail the process of bringing a previously developed photochemical benzylic bromination, utilizing in situ bromine generation, from lab to pilot scale. The process setup is discussed in detail, alongside a comprehensive risk assessment and discussion of problems encountered in the investigation of key reaction parameters. Ultimately, an assay yield of 88% was obtained in 22 s irradiated residence time, resulting in a productivity of 4.1 kg h(-1) (space-time yield = 82 kg L-1 h(-1)) representing a 14-fold scale-up versus the lab-scale process.
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