The author of 《Novel preparation of N-arylmethyl-N-arylmethyleneamine N-oxides from benzylic bromides with zinc and isobutyl nitrite》 were Yanai, Kei; Togo, Hideo. And the article was published in Tetrahedron in 2019. Category: chlorides-buliding-blocks The author mentioned the following in the article:
Treatment of benzylic bromides with Zn and LiCl, followed by the reaction with i-Bu nitrite gave N-arylmethyl-N-arylmethyleneamine N-oxides in moderate yields [e.g., 4-methylbenzyl bromide → I (47%)]. The present reaction is a novel and simple method for the preparation of nitrones from benzylic bromides, although the yields are moderate. The experimental process involved the reaction of 1-(Bromomethyl)-4-chlorobenzene(cas: 622-95-7Category: chlorides-buliding-blocks)
1-(Bromomethyl)-4-chlorobenzene(cas: 622-95-7) undergoes carbonylation in the presence of dimer of chloro(1,5-cyclooctadiene)rhodium(I) to yield the corresponding phenylacetic acid.Category: chlorides-buliding-blocks It can be synthesized by reacting 4-chlorobenzyl alcohol with bromodimethylsulfonium bromide (BDMS) It can also be synthesized by refluxing a mixture of 4-chlorobenzaldehyde, chlorotrimethylsilane, 1,1,3,3-tetramethyldisiloxane and lithium bromide.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics