Benzoic acid, 5-chloro-2-ethenyl-, methyl ester

Base Information

• Chemical Name: Benzoic acid, 5-chloro-2-ethenyl-, methyl ester
• CAS No.: 131001-88-2
• Molecular Formula: C10H9ClO2
• Molecular Weight: 196.633
• Mol file: 131001-88-2.mol

Synonyms:

Chemical Property of Benzoic acid, 5-chloro-2-ethenyl-, methyl ester

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzoic acid, 5-chloro-2-ethenyl-, methyl ester

There total 6 articles about Benzoic acid, 5-chloro-2-ethenyl-, methyl ester 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: 91.0%

methyl-2-bromo-5-chlorobenzoate (27007-53-0) + potassium vinyltrifluoroborate → methyl 2-ethenyl-5-chlorobenzoate (131001-88-2)

Guidance literature:

With caesium carbonate; triphenylphosphine; palladium dichloride; In tetrahydrofuran; water; at 85 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201804152

Reference yield: 75.0%

ethene (74-85-1) + methyl-2-bromo-5-chlorobenzoate (27007-53-0) → methyl 2-ethenyl-5-chlorobenzoate (131001-88-2)

Guidance literature:

With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In acetonitrile; at 120 ℃; for 24h; under 22800 Torr;

Reference yield:

2-bromo-5-chlorobenzoic acid (21739-93-5) → methyl 2-ethenyl-5-chlorobenzoate (131001-88-2)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; toluene; diethyl ether / 2 h / Inert atmosphere; Schlenk technique

2: caesium carbonate; palladium dichloride; triphenylphosphine / tetrahydrofuran; water / 0.4 h / 85 °C / Inert atmosphere; Schlenk technique

With caesium carbonate; triphenylphosphine; palladium dichloride; In tetrahydrofuran; methanol; diethyl ether; water; toluene;

DOI:10.1002/anie.201209582

upstream raw materials:

ethene

methyl-2-bromo-5-chlorobenzoate

2-bromo-5-chlorobenzoic acid

pinacol vinylboronate

Downstream raw materials:

2-<(4-chloro-2-methoxycarbonylphenyl)methyl>-1,3-dioxane

5-CHLORO-2-(3-OXOPROPYL)-BENZOIC ACID

methyl 5-chloro-2-formylbenzoate

Refernces

• 1、 Wei, Wen-tao,Chen, Zhen-yu,Lin, Yong-lu,Chen, Ri-xing,Wang, Qi,Wu, Qing-guang,Liu, Si-jun,Yan, Ming,Zhang, Xue-jing. "Synthesis of Isoindolinones through Intramolecular Amidation of ortho-Vinyl Benzamides". supporting information. p. 1972 - 1976. Retrieved 2020/04/20.
• 2、 Chen, Zhen-Yu,Wu, Liang-Yu,Fang, Hai-Sheng,Zhang, Ting,Mao, Zhi-Feng,Zou, Yong,Zhang, Xue-Jing,Yan, Ming. "Intramolecular Hydroamidation of ortho-Vinyl Benzamides Promoted by Potassium tert-Butoxide/N,N-Dimethylformamide". supporting information. p. 3894 - 3899. Retrieved 2017/10/07.