This method is suitable for the preparation of a wide variety of unsymmetric ethers. The nucleophilic substitution of halides with alkoxides leads to the desired products.
If the halides are sterically demanding and there are accessible protons in the β-position, the alkoxide will act as a base, and side products derived from elimination are isolated instead.
Mechanism of the Williamson Synthesis
Zn- and Cu-Catalyzed Coupling of Tertiary Alkyl Bromides and Oxalates to Forge Challenging C-O, C-S, and C-N Bonds
Y. Gong, Z. Zhu, Q. Qian, W. Zong, H. Gong, Org. Lett., 2021, 23, 1005-1010.