Synthesis of meta,meta-bridged biaryls [7,0-metacyclophanes] via aryl-aryl coupling: factors affecting the cyclization was written by Mohamed, Salah E. N.;Whiting, Donald A.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1983.Synthetic Route of C10H13BrO This article mentions the following:
Isoxazoline I and 3,4-I(MeO)C6H3(CH2)4CH(OAc)(CH2)2C6H3(OMe)I-4,3 were prepared; on treatment with (Ph3P)4Ni in DMF at 55-65° for 48 h these compounds cyclized to the [7.0]metacyclophanes II and III, resp., in 31 and 49% yield, resp. The analog 3,4-I(MeO)C6H3(CH2)4SO2(CH2)3C6H3(OMe)I-4,3 was also prepared; it failed to cyclize. Steric effects at the coupling site are more important than torsional strain in the products in determination of the product yield. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Synthetic Route of C10H13BrO).
1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbonbromine bond is electrophilic in nature. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Synthetic Route of C10H13BrO
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary