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제124회 대한화학회 학술발표회, 총회 및 기기전시회 안내 From p-Xylene to Ibuprofen in Flow: 3-Step Synthesis via Unified Sequence of Chemoselective C–H Metalations

등록일
2019년 8월 27일 14시 37분 38초
접수번호
1647
발표코드
ORGN.P-424 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 18일 (금요일) 11:00~12:30
발표형식
포스터
발표분야
Organic Chemistry
저자 및
공동저자
Hyune-Jea Lee, Heejin Kim1,*, Dong Pyo Kim*
Department of Chemical Engineering, Pohang University of Science and Technology, Korea
1Department of Chemistry, Korea University, Korea

Ibuprofen was prepared from an inactive and low-cost p‐xylene by three‐step flow synthesis through chemoselective metalations of benzyl positions using an in situ generated LICKOR‐type superbase. The flow approach in the microreactor facilitated the comprehensive exploration of over 100 conditions in the first reaction step by varying concentrations, temperatures, solvents, and equivalents of reagents, enabling optimal conditions to be found with 95 % yield by significantly suppressing the competitive side reaction resulting in byproducts, followed by the second C−H metalation step in 95 % yield. Moreover, gram‐scale synthesis of ibuprofen in the final step was achieved by biphasic flow reaction of solution‐phase intermediate with gas phase carbon dioxide, isolating 2.3 g for 10 min of operation time.


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