Chemical Properties
1-Bromo-2-isopropylbenzene is an orange-yellow transparent liquid at room temperature, with very good stability and reactivity, substitution reaction, addition reaction and so on.
Uses
1-Bromo-2-(1-methylethyl)benzene serves as a precursor for synthesizing 2-isopropylbenzaldehyde via reaction with lithium metal and N,N-dimethylformamide, and for preparing 2-(2-isopropylphenyl)pyridine derivatives through coupling with tert-butyllithium, 2-(2-isopropylphenyl)pyridine, and pyridine[1].
Synthesis
1-Bromo-2-(1-methylethyl)benzene is synthesised using 1-bromo-2-isopropenylbenzene as a raw material by chemical reaction. The specific synthesis steps are as follows:
General procedure: The mixture of S-3 (1 equivalent), TsNHNH2 (5 equivalent), NaOAc·3H2O (5equivalent), and THF (0.3 M) were heated at reflux for 24 h. When the reaction wascomplete as determined by TLC, cooling to room temperature and adding H2O. Thecrude mixture was extracted with EtOAc (3x20 mL) and the combined organicextracts were washed with brine, dried over anhydrous Na2SO4, and concentrated invacuo. The crude was then purified by column chromatography (Petroleum ether) onsilicagel to give 1-Bromo-2-(1-methylethyl)benzene as a colorless oil.
References
[1] Mazzanti, A., Lunazzi, L., Lepri, S., Ruzziconi, R., & Schlosser, M. (2011). How Space‐Filling Is a Pyridine Lone Pair? European Journal of Organic Chemistry, 2011(33), 6725–6731.
https://doi.org/10.1002/ejoc.201101008
