Integrated micro flow synthesis based on sequential Br-Li exchange reactions of p-, m-, and o-dibromobenzenes
- Authors
- 김희진
- Issue Date
- 12월-2007
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- arenes; flow reactions; integrated micro flow synthesis; lithiation; microreactors
- Citation
- CHEMISTRY-AN ASIAN JOURNAL, v.2, no.12, pp.1513 - 1523
- Indexed
- SCOPUS
- Journal Title
- CHEMISTRY-AN ASIAN JOURNAL
- Volume
- 2
- Number
- 12
- Start Page
- 1513
- End Page
- 1523
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/140060
- DOI
- 10.1002/asia.200700231
- ISSN
- 1861-4728
- Abstract
- A micro flow system consisting of micromixers and microtube reactors provides an effective method for the introduction of two electrophiles onto p-, m-, and o-dibromobenzenes. The Br-Li exchange reaction of p-dibromobenzene with nBuLi can be conducted by using the micro flow system at 20 degrees C, although much lower temperatures (< -48 degrees C) are needed for a batch reaction. The resulting p-bromophenyllithium was allowed to react with an electrophile in the micro flow system at 20 degrees C. The p-substituted bromobenzene thus obtained was subjected to a second Br-Li exchange reaction followed by reaction with a second electrophile at 20 degrees C in one flow. A similar transformation can be carried out with m-dibromobenzene by using the micro flow system. However, the Br-Li exchange reaction of o-dibromobenzene followed by reaction with an electrophile should be conducted at -78 degrees C to avoid benzyne formation. The second Br-Li exchange reaction followed by reaction with an electrophile can be carried out at 0 degrees C. By using the present method, a variety of p-, m-, and o-disubstituted benzenes were synthesized in one flow at much higher temperatures than are required for conventional batch reactions.
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