Fraser, Cassandra L.; Anastasi, Natia R.; Lamba, Jaydeep J. S. published their research in Journal of Organic Chemistry on December 26 ,1997. The article was titled 《Synthesis of Halomethyl and Other Bipyridine Derivatives by Reaction of 4,4′-Bis[(trimethylsilyl)methyl]-2,2′-bipyridine with Electrophiles in the Presence of Fluoride Ion》.Synthetic Route of C12H10Cl2N2 The article contains the following contents:
This report describes a new, high yield route to bipyridine derivatives via a trimethylsilyl (TMS) intermediate. 4,4′-Dimethyl-2,2′-bpy was reacted with lithium diisopropylamide, and the dianion thus formed was trapped with TMSCl to generate 4,4′-bis[(trimethylsilyl)methyl]-2,2′-bpy. The TMS group was removed using dry F- sources (TBAF/SiO2 in THF or CsF in DMF) in the presence of BrF2CCF2Br or Cl3CCCl3 to produce the bromide or chloride analogs of 4,4′-bis(halomethyl)-2,2′-bipyridine, resp. The CsF/DMF methodol. extends to other electrophiles, including benzaldehyde to give 4,4′-bis(2-hydroxy-2-phenethyl)-2,2′-bpy as well as to alkyl halides. Benzyl Br, dodecyl Br, and α-chloroacetonitrile gave mixtures of di- and monoalkylated products along with the diprotonated product, 4,4′-dimethyl-2,2′-bpy. In the experiment, the researchers used 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Synthetic Route of C12H10Cl2N2)
4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Synthetic Route of C12H10Cl2N2 Pyridine has a conjugated system of six π electrons that are delocalized over the ring.