Original Article:
Exploring Possible Surrogates for Kobayashi’s Aryne Precursors
Ana Carolina A. Muraca, et al.
ACS Omega, 2020, 5, 5, 2440–2457.
10.1021/acsomega.9b03989
1-Chlorobutane is often used as organic synthesis raw materials, pharmaceutical intermediates, solvents (such as HPLC solvents) and dewaxing agents, etc. 1-Chlorobutane is one of the commonly used alkylating reagents in the synthesis of organic and organometallic compounds. For example, the standard preparation of n-butyllithium (nBuLi) is the reaction of 1-chlorobutane with lithium metal. More applications of 1-chlorobutane are being discovered and explored by scientists.
In this work, the researchers provide interesting insight into the mechanism of formation of a class of arynes, involving a reaction pathway for the preparation of 1-azidobutane from 1-chlorobutane. The reaction process is shown in the figure. When compound 24 is 1-chlorobutane, the reaction product is compound 1-azidobutane (25d). The specific synthesis procedures include:
1. Add 1-chlorobutane (R-X), sodium azide (NaN3), and DMSO to a flask, then keep the resulting mixture under anhydrous conditions and magnetically stir at room temperature for 14 hours.
2. Add ice-cold distilled water to the mixture and extract with ether.
3. The organic phase was washed with saturated sodium bicarbonate solution and dried over MgSO4.
4. After filtration, the solvent was evaporated under reduced pressure to give azide 25d (1-azidobutane).
