Optimizacija Sonogashirove reakcije med 4-bromoacetofenonom in 4-etinil-N,N-dimetilanilinom

Turk, Matevž (author), Košmrlj, Janez (mentor)

V sklopu diplomskega dela smo optimizirali reakcijske pogoje Sonogashirove reakcije med 4-bromoacetofenonom in 4-etinil-N,N-dimetilanilinom ter postopek izolacije nastalega produkta. Našli smo kombinacijo reakcijskih pogojev in mobilne faze za čiščenje produkta s preparativno kolonsko kromatografijo, s katero smo uspešno presegli zadan cilj 80% izkoristka. Optimiziran postopek smo preizkusili še na večji skali. 1-[4-[2-[4-(Dimetilamino)fenil]etinil]fenil]etanon, sintetiziran tekom optimizacije, smo dodatno očistili s preparativno kolonsko kromatografijo in okarakterizirali z 1H NMR, 13C NMR, IR in masno spektroskopijo, mu izmerili tališče ter določili njegovo čistost s HPLC.

• Language: Slovenian
• Keywords: Sonogashirova reakcija, 4-bromoacetofenon, 4-etinil-N, N-dimetilanilin
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2022
• PID: 20.500.12556/RUL-139479
• COBISS.SI-ID: 125498627
• Publication date in RUL: 02.09.2022

Secondary language

• Language: English
• Title: Optimisation of the Sonogashira reaction between 4-bromoacetophenone and 4-ethynyl-N,N-dimethylaniline

Abstract

As a part of my Bachelor's thesis we have optimised reaction conditions of the Sonogashira reaction between 4-bromoacetophenone and 4-ethynyl-N,N-dimethylaniline, and the isolation process of the formed product. We have discovered a combination of reaction conditions and a mobile phase, used in purification of the formed product by the means of preparative column cromatography, with which we have successfuly surpassed our goal of an 80% yield. We have further tested the optimised procedure on a larger scale. 1-[4-[2-[4-(Dimethylamino)phenyl]etinyl]phenyl]ethanone, synthesized during the optimization process, has been further purified using preparative column cromatography, and characterized by 1H NMR, 13C NMR, IR and mass spectroscopy, measuring of its melting point and determining its purity by HPLC.

• Keywords: Sonogashira reaction, 4-bromoacetophenone, ethynyl-N, N-dymethylamine