2-Propenoic acid, 3-(4-bromophenyl)-3-phenyl-, ethyl ester, (E)-

Base Information

• Chemical Name: 2-Propenoic acid, 3-(4-bromophenyl)-3-phenyl-, ethyl ester, (E)-
• CAS No.: 183593-80-8
• Molecular Formula: C17H15BrO2
• Molecular Weight: 331.209
• Mol file: 183593-80-8.mol

Synonyms:

Chemical Property of 2-Propenoic acid, 3-(4-bromophenyl)-3-phenyl-, ethyl ester, (E)-

Chemical Property:

• PSA: 26.30000
• LogP: 4.44390

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Propenoic acid, 3-(4-bromophenyl)-3-phenyl-, ethyl ester, (E)-

There total 9 articles about 2-Propenoic acid, 3-(4-bromophenyl)-3-phenyl-, ethyl ester, (E)- 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: 83.0%

4-bromobenzenediazonium tetrafluoroborate (673-40-5) + ethyl cinnamate (4192-77-2) → 3-(4-bromo-phenyl)-3-phenyl-acrylic acid ethyl ester (183593-80-8)

Guidance literature:

With palladium diacetate; In 1-butyl-3-methylimidazolium Tetrafluoroborate; at 70 - 80 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.02.021

Reference yield:

iodobenzene (591-50-4) + ethyl (E)-3-(4-bromophenyl)-2-propenoate (24393-53-1,136265-11-7,15795-20-7) → 3-(4-bromo-phenyl)-3-phenyl-acrylic acid ethyl ester (183593-80-8) + (Z)-3-(4-bromo-phenyl)-3-phenyl-acrylic acid ethyl ester (183593-81-9)

Guidance literature:

With tetrabutylammomium bromide; sodium hydrogencarbonate; palladium diacetate; In N,N-dimethyl-formamide; at 60 ℃; for 3h; Yield given. Yields of byproduct given;

DOI:10.1016/0040-4039(96)01608-5

Reference yield:

1,4-bromoiodobenzene (589-87-7) → 3-(4-bromo-phenyl)-3-phenyl-acrylic acid ethyl ester (183593-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / NEt₃ / PdCl₂(PPh₃)2 / acetonitrile / 1 h / 80 °C

2: NaHCO₃, n-Bu₄NBr / Pd(OAc)2 / dimethylformamide / 3 h / 60 °C

With tetrabutylammomium bromide; sodium hydrogencarbonate; triethylamine; bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(96)01608-5

upstream raw materials:

iodobenzene

ethyl (E)-3-(4-bromophenyl)-2-propenoate

diethoxyphosphoryl-acetic acid ethyl ester

(4-bromophenyl)(phenyl)methanone

Downstream raw materials:

(Z)-3-(4-bromo-phenyl)-3-phenyl-prop-2-en-1-ol

(E)-3-(4-bromophenyl)-3-phenylacrylic acid

(E)-3-[4-(3-dimethylamino-prop-1-ynyl)-phenyl]-3-phenyl-acrylic acid ethyl ester

(E)-(2S)-3-{4-[3-(4-Bromophenyl)-3-phenyl-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester

Refernces

• 1、 Li, Yang,Dong, Kaiwu,Wang, Zheng,Ding, Kuiling. "Rhodium(I)-catalyzed enantioselective hydrogenation of substituted acrylic acids with sterically similar β,β-diaryls". supporting information. p. 6748 - 6752. Retrieved 2013/07/26.
• 2、 Mogensen, John P.,Jeppesen, Lone,Bury, Paul S.,Pettersson, Ingrid,Fleckner, Jan,Nehlin, Jan,Frederiksen, Klaus S.,Albrektsen, Tatjana,Din, Nanni,Mortensen, Steen B.,Svensson, L. Anders,Wassermann, Karsten,Wulff, Erik M.,Ynddal, Lars,Sauerberg, Per. "Design and synthesis of novel PPARα/γ/δ triple activators using a known PPARα/γ dual activator as structural template". . p. 257 - 260. Retrieved 2007/10/03.