Nucleophilic Cl- Reagents
Mechanism + Description
Typically SN2 with displacement of another halogen (Iodide) or leaving group (sulphonate, nitro), etc. Also via reaction of Cl- with other electrophiles, like diazonium salts. Chlroride anions can add to radical iminium cations as well.
Normally, simple bromide salts like Na/K/Li Chloride, or tetralkyl ammonium or phosphonium chlorides like nBu4NCl, are used. Hydrogen chloride is typically used for deoxychlorination, but can be used to add HCl to unsaturated C-C bonds and epoxides, etc. The Sandmeyer reaction can be used to make aryl chlorides from anilines.
Fortt, R.; Wootton, R. C. R.; De Mello, A. J. Continuous-Flow Generation of Anhydrous Diazonium Species: Monolithic Microfluidic Reactors for the Chemistry of Unstable Intermediates. Org. Process Res. Dev. 2003, 7(5), 762–768.
Relevant scale up example
Org. Process Res. Dev. 2010, 14, 562–567.
26 kg scale