ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-bromocinnamate

Base Information

• Chemical Name: ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-bromocinnamate
• CAS No.: 540779-19-9
• Molecular Formula: C₃₄H₃₅BrO₃
• Molecular Weight: 571.554
• Mol file: 540779-19-9.mol

Synonyms:ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-bromocinnamate

Chemical Property of ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-bromocinnamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-bromocinnamate

There total 5 articles about ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-bromocinnamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-aminocinnamate (1352042-73-9) → ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-bromocinnamate (540779-19-9)

Guidance literature:

With 1-hexyl nitrite; Bromoform; at 95 - 100 ℃; for 5.08333h; Inert atmosphere;

DOI:10.1021/jm2011436

Reference yield:

ethyl (E)-3-bromo-4-(trifluoromethanesulfonyloxy)cinnamate (540779-18-8) + 3-(1-adamantyl)-4-benzyloxyphenylboronic acid (221137-01-5) → ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-bromocinnamate (540779-19-9)

Guidance literature:

Reference yield:

ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-nitrocinnamate (1352042-59-1) → ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-bromocinnamate (540779-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tin(II) chloride hydrate / ethanol / 2 h / 80 °C / Inert atmosphere

2: 1-hexyl nitrite; Bromoform / 5.08 h / 95 - 100 °C / Inert atmosphere

With tin(II) chloride hydrate; 1-hexyl nitrite; Bromoform; In ethanol;

DOI:10.1021/jm2011436

upstream raw materials:

ethyl (E)-3-bromo-4-(trifluoromethanesulfonyloxy)cinnamate

3-(1-adamantyl)-4-benzyloxyphenylboronic acid

ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-nitrocinnamate

ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-aminocinnamate

Downstream raw materials:

ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-bromocinnamate

(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-bromocinnamic acid