Abstract: To address the gap in undergraduate experimental teaching regarding safe and effective electrophilic fluorination, we have developed a comprehensive chemical experiment focused on the synthesis and characterization of fluorine-containing fine chemical intermediates. The experiment utilizes N-hydroxyphthalimide (NHPI) as a catalyst and 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt (Selectfluor) as an electrophilic fluorination reagent. This approach enables highly selective electrophilic fluorination of the tetrahydroquinoline aromatic ring under mild conditions, with the product characterized by infrared spectroscopy (IR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS). The experiment provides a comprehensive training platform for students, enhancing their theoretical understanding and experimental skills in organic synthesis, separation and purification, and structural characterization. It embodies the elements of comprehensiveness, innovation, and practical application, aligning with the development goals of the fine chemical engineering curriculum. Through this experimental module, students gain hands-on experience in the preparation of fluorine-containing fine chemicals, broaden their professional perspectives, and develop critical thinking, problem-solving skills, and a mindset oriented towards scientific research and innovation.

Key words: Comprehensive experiment, Electrophilic fluorination reaction, Fluorine-containing fine chemical intermediate, Semi-micro synthesis