622-24-2Relevant articles and documents
Preparation method of P-chloromethyl styrene
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Paragraph 0054-0066, (2021/05/01)
The invention relates to the field of organic chemistry, in particular to a preparation method of p-chloromethyl styrene. The invention provides a preparation method of p-chloromethyl styrene, which comprises the following step: carrying out elimination reaction on 1-(2-chloroethyl)-4-chloromethylbenzene under alkaline conditions to prepare the p-chloromethyl styrene. According to the preparation method, the reaction raw materials with relatively low price are utilized, the manufacturing cost is reduced, the manufacturing process is simple and safe, various side reactions are less, the product conversion rate is high, the purity is high, and thus a good industrialization prospect can be realized.
N -Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N -chlorosuccinimide
Li, Zi-Hao,Fiser, Béla,Jiang, Biao-Lin,Li, Jian-Wei,Xu, Bao-Hua,Zhang, Suo-Jiang
supporting information, p. 3403 - 3408 (2019/04/01)
The direct chlorination of C-H bonds has received considerable attention in recent years. In this work, a metal-free protocol for hydrocarbon C-H bond chlorination with commercially available N-chlorosuccinimide (NCS) catalyzed by N-hydroxyphthalimide (NHPI) with 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) functioning as an external radical initiator is presented. Aliphatic and benzylic substituents and also heteroaromatic ones were found to be well tolerated. Both the experiments and theoretical analysis indicate that the reaction goes through a process wherein NHPI functions as a catalyst rather than as an initiator. On the other hand, the hydrogen abstraction of the C-H bond conducted by a PINO species rather than the highly reactive N-centered radicals rationalizes the high chemoselectivity of the monochlorination obtained by this protocol as the latter is reactive towards the C(sp3)-H bonds of the monochlorides. The present results could hold promise for further development of a nitroxy-radical system for the highly selective functionalization of the aliphatic and benzylic hydrocarbon C-H.
Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling
Longwitz, Lars,Jopp, Stefan,Werner, Thomas
, p. 7863 - 7870 (2019/06/27)
A catalytic system for the chlorination of alcohols under Appel conditions was developed. Benzotrichloride is used as a cheap and readily available chlorinating agent in combination with trioctylphosphane as the catalyst and phenylsilane as the terminal reductant. The reaction has several advantages over other variants of the Appel reaction, e.g., no additional solvent is required and the phosphane reagent is used only in catalytic amounts. In total, 27 different primary, secondary, and tertiary alkyl chlorides were synthesized in yields up to 95%. Under optimized conditions, it was also possible to convert epoxides and an oxetane to the dichlorinated products.