Quality Control of Ethyl 3-(4-chlorophenyl)propanoateOn November 4, 1998 ,《Ni(II)-Catalyzed Cross-Coupling between Polyfunctional Arylzinc Derivatives and Primary Alkyl Iodides》 appeared in Journal of the American Chemical Society. The author of the article were Giovannini, Riccardo; Knochel, Paul. The article conveys some information:
A novel nickel-catalyzed coupling reaction of arylzinc bromides ArZnBr (Ar = Ph, 4-ClC6H4, 4-MeOC6H4, 4-NCC6H4, 3-EtO2CC6H4, 2-EtO2CC6H4), generated from the aryl iodides, and functionalized primary alkyl iodides R(CH2)nI (n = 2,3,5; R = Me3CCOO, 2-methyl-1,3-dithiolanyl, EtO2C, BuCO, PhS, (CH2)5NCO) to give aralkyl derivative Ar(CH2)nR in 71-80% yield. Arylzinc bromides are generated from aryl iodides by either treatment of the iodide with Me2CHMgBr in THF followed by addition of ZnBr2 to the Grignard reagent, or by treatment of the aryl iodide with BuLi and addition of ZnBr2. E.g., 4-cyanophenylzinc bromide is formed by transmetalation of 4-NCC6H4I at -90° with BuLi in THF and addition of ZnBr2; the arylzinc bromide was then concentrated and added to a THF solution containing 10 mol% Ni(acac)2, 1 equivalent 4-F3CC6H4CH:CH2, and 1 equivalent Me(SCH2CH2S)CH2CH2I to give I in 80% yield. The absence of 4-F3CC6H4CH:CH2 leads to formation of products formed form homocoupling and zinc-iodine transmetalation of the alkyl iodides. The coupling tolerates ketone, amide, ester, and nitrile functionality and allows coupling of sp2-aryl and sp3-alkyl groups fro which few coupling methods exist. After reading the article, we found that the author used Ethyl 3-(4-chlorophenyl)propanoate(cas: 7116-36-1Quality Control of Ethyl 3-(4-chlorophenyl)propanoate)
Ethyl 3-(4-chlorophenyl)propanoate(cas: 7116-36-1) belongs to organochlorine compounds. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. Quality Control of Ethyl 3-(4-chlorophenyl)propanoate The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics