Dimethyl 2-(4-bromophenyl)succinate

Base Information

• Chemical Name: Dimethyl 2-(4-bromophenyl)succinate
• CAS No.: 97728-47-7
• Molecular Formula: C₁₂H₁₃BrO₄
• Molecular Weight: 301.137
• DSSTox Substance ID: DTXSID701265602
• Mol file: 97728-47-7.mol

Synonyms:dimethyl 2-(4-bromophenyl)succinate;dimethyl 2-(4-bromophenyl)butanedioate;97728-47-7;DTXSID701265602;1,4-Dimethyl 2-(4-bromophenyl)butanedioate

Chemical Property of Dimethyl 2-(4-bromophenyl)succinate

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 299.99972
• Heavy Atom Count: 17
• Complexity: 272

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CC(C1=CC=C(C=C1)Br)C(=O)OC

Technology Process of Dimethyl 2-(4-bromophenyl)succinate

There total 4 articles about Dimethyl 2-(4-bromophenyl)succinate 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: 96.0%

methanol (67-56-1) + 1-bromo-4-ethenyl-benzene (2039-82-9) + carbon monoxide (201230-82-2) → dimethyl 2-(4-bromophenyl)succinate (97728-47-7)

Guidance literature:

methanol; With palladium(II) trifluoroacetate; bis(9-anthryl)-2,3-dimethyl-1,4-diazabutadiene; toluene-4-sulfonic acid; p-benzoquinone; In tetrahydrofuran; for 0.166667h; Schlenk technique; Inert atmosphere; Autoclave;

1-bromo-4-ethenyl-benzene; carbon monoxide; In tetrahydrofuran; at 20 ℃; for 66h; under 3000.3 Torr; Schlenk technique; Inert atmosphere; Autoclave;

DOI:10.1002/adsc.201400501

Reference yield: 86.0%

methanol (67-56-1) + 4-bromo-1-ethynylbenzene (766-96-1) + carbon monoxide (201230-82-2) → dimethyl 2-(4-bromophenyl)succinate (97728-47-7)

Guidance literature:

With 1,3-bis(tert-butyl(pyridin-2-yl)phosphanyl)propane; palladium(II) acetylacetonate; toluene-4-sulfonic acid; at 100 ℃; for 20h; under 30003 Torr; chemoselective reaction; Sealed tube;

DOI:10.1021/jacs.8b05852

Reference yield: 86.0%

4-oxo-4-(4-bromophenyl)butanoic acid (6340-79-0) + trimethyl orthoformate (149-73-5) → dimethyl 2-(4-bromophenyl)succinate (97728-47-7)

Guidance literature:

With perchloric acid; thallium(III) nitrate; for 4h; Ambient temperature;

upstream raw materials:

4-oxo-4-(4-bromophenyl)butanoic acid

trimethyl orthoformate

methanol

1-bromo-4-ethenyl-benzene

Refernces

• 1、 Liu, Jiawang,Dong, Kaiwu,Franke, Robert,Neumann, Helfried,Jackstell, Ralf,Beller, Matthias. "Selective Palladium-Catalyzed Carbonylation of Alkynes: An Atom-Economic Synthesis of 1,4-Dicarboxylic Acid Diesters". supporting information. p. 10282 - 10288. Retrieved 2018/08/03.
• 2、 Fini, Francesco,Beltrani, Michela,Mancuso, Raffaella,Gabriele, Bartolo,Carfagna, Carla. "Selective aryl α-diimine/palladium-catalyzed bis-alkoxycarbonylation of olefins for the synthesis of substituted succinic diesters". . p. 177 - 184. Retrieved 2015/01/30.