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

Base Information

• Chemical Name: ethyl (E)-4-bromo-3-(trifluoromethyl)cinnamate
• CAS No.: 1352042-48-8
• Molecular Formula: C₁₂H₁₀BrF₃O₂
• Molecular Weight: 323.109
• Mol file: 1352042-48-8.mol

Synonyms:

Chemical Property of ethyl (E)-4-bromo-3-(trifluoromethyl)cinnamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (E)-4-bromo-3-(trifluoromethyl)cinnamate

There total 2 articles about ethyl (E)-4-bromo-3-(trifluoromethyl)cinnamate 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: 80.0%

1-bromo-4-iodo-2-(trifluoromethyl)benzene (364-11-4) + ethyl acrylate (140-88-5,9003-32-1) → ethyl (E)-4-bromo-3-(trifluoromethyl)cinnamate (1352042-48-8)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; at 115 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm2011436

Reference yield:

4-bromo-3-(trifluoromethyl)aniline (393-36-2) → ethyl (E)-4-bromo-3-(trifluoromethyl)cinnamate (1352042-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sulfuric acid; sodium nitrite / water / 0.97 h / 0 - 5 °C

1.2: 2.3 h / 0 - 100 °C

2.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / 3 h / 115 °C / Inert atmosphere

With sulfuric acid; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; sodium nitrite; In water; 2.1: Mizoroki-Heck reaction;

DOI:10.1021/jm2011436

Reference yield: 94.0%

ethyl (E)-4-bromo-3-(trifluoromethyl)cinnamate (1352042-48-8) + 3-(1-adamantyl)-4-benzyloxyphenylboronic acid (221137-01-5) → ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-(trifluoromethyl)cinnamate (1352042-55-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; for 18h; Reflux; Inert atmosphere;

DOI:10.1021/jm2011436

upstream raw materials:

1-bromo-4-iodo-2-(trifluoromethyl)benzene

ethyl acrylate

4-bromo-3-(trifluoromethyl)aniline

Downstream raw materials:

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

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

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

Refernces