methyl (E)-4-(4-chlorophenyl)-3-methoxycarbonylbut-3-enoate

Base Information

• Chemical Name: methyl (E)-4-(4-chlorophenyl)-3-methoxycarbonylbut-3-enoate
• CAS No.: 74531-19-4
• Molecular Formula: C₁₃H₁₃ClO₄
• Molecular Weight: 268.697
• Mol file: 74531-19-4.mol

Synonyms:methyl (E)-4-(4-chlorophenyl)-3-methoxycarbonylbut-3-enoate

Chemical Property of methyl (E)-4-(4-chlorophenyl)-3-methoxycarbonylbut-3-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-4-(4-chlorophenyl)-3-methoxycarbonylbut-3-enoate

There total 11 articles about methyl (E)-4-(4-chlorophenyl)-3-methoxycarbonylbut-3-enoate 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: 93.0%

p-chlorobenzenediazonium tetrafluoroborate (673-41-6) + Dimethyl itakonate (617-52-7) → methyl (E)-4-(4-chlorophenyl)-3-methoxycarbonylbut-3-enoate (74531-19-4)

Guidance literature:

Dimethyl itakonate; With aluminum oxide; palladium diacetate; In methanol; at 25 ℃; for 0.5h;

p-chlorobenzenediazonium tetrafluoroborate; In methanol; at 25 ℃; for 0.833333h;

DOI:10.1002/ejoc.201901708

Reference yield: 87.0%

1-Chloro-4-iodobenzene (637-87-6) + Dimethyl itakonate (617-52-7) → methyl (E)-4-(4-chlorophenyl)-3-methoxycarbonylbut-3-enoate (74531-19-4)

Guidance literature:

With silver(I) acetate; palladium diacetate; In acetic acid; at 110 ℃; for 3h; Inert atmosphere;

DOI:10.1002/aoc.4159

Reference yield: 84.8%

4-chlorobenzyl bromide (622-95-7) + dimethylfumarate (624-49-7) → methyl (E)-4-(4-chlorophenyl)-3-methoxycarbonylbut-3-enoate (74531-19-4)

Guidance literature:

With tributylphosphine; caesium carbonate; In toluene; at 60 ℃; for 48h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.1c01214

upstream raw materials:

dimethyl 2-(diethoxyphosphoryl)succinate

4-chlorobenzaldehyde

dimethyl cis-but-2-ene-1,4-dioate

bis(2,2,2-trifluoroethyl)phosphite

Downstream raw materials:

((E)-4-chloro-benzylidene)-succinic acid

2-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-3-cyclohexylidene-succinic acid

2-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-3-cyclohexylidene-succinic acid 4-methyl ester

Refernces

• 1、 Yan, Tingting,Babu, Kaki Raveendra,Wu, Yong,Li, Yang,Tang, Yuhai,Xu, Silong. "Phosphine-Catalyzed Cross-Coupling of Benzyl Halides and Fumarates". supporting information. p. 4570 - 4574. Retrieved 2021/06/28.
• 2、 Bangar, Pronnoy G.,Jawalkar, Priyanka R.,Dumbre, Swapnil R.,Patil, Dharmaraj J.,Iyer, Suresh. "Silver sequestration of halides for the activation of Pd(OAc)2 catalyzed Mizoroki-Heck reaction of 1,1 and 1,2 - Disubstituted alkenes". . . Retrieved 2017/11/23.