Meng, He; Bai, Shiming; Qiao, Yu; He, Ting; Li, Weiyi; Ming, Jialin published an article in 2022. The article was titled 《Rhodium-Catalyzed Three-Component Reaction of Alkynes, Arylzinc Chlorides, and Iodomethanes Producing Trisubstituted/Tetrasubstituted Alkenes with/without 1,4-Migration》, and you may find the article in Organic Letters.Synthetic Route of C7H5BrO2 The information in the text is summarized as follows:
A three-component reaction of alkynes, arylzinc chlorides and iodomethanes was found to proceed in the presence of a rhodium catalyst to give high yields of trisubstituted/tetrasubstituted alkenes I [R = 2-MeC6H4, 2-Me-4-MeOC6H3, 2-furyl, etc.; R1 = H, Me; R2 = Me, n-Pr, (CH2)4I, etc.; R3 = Me, n-Pr, (CH2)3OMe, etc.; R2R3 = (CH2)10]. The usual arylzinc chlorides only gave trisubstituted alkenes, generated through a migratory carbozincation-cross-coupling sequence, where 1,4-Rh migration from an alkenyl carbon to an aryl carbon occurred. In contrast, 5-membered heteroarylzinc chlorides only gave the tetrasubstituted alkenes via a carborhodation-cross-coupling pathway without 1,4-migration. The experimental part of the paper was very detailed, including the reaction process of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4Synthetic Route of C7H5BrO2)
Furthermore, the coupling of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4) with β-methallyl alcohol was catalyzed by Pd(OAc)2 in combination with P(t-Bu)3.Synthetic Route of C7H5BrO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary