3-(4-bromo-phenyl)-2-cyano-4-methylene-pentanedioic acid 1-ethyl ester 5-methyl ester

Base Information

• Chemical Name: 3-(4-bromo-phenyl)-2-cyano-4-methylene-pentanedioic acid 1-ethyl ester 5-methyl ester
• CAS No.: 910641-57-5
• Molecular Formula: C₁₆H₁₆BrNO₄
• Molecular Weight: 366.211
• Mol file: 910641-57-5.mol

Synonyms:3-(4-bromo-phenyl)-2-cyano-4-methylene-pentanedioic acid 1-ethyl ester 5-methyl ester

Chemical Property of 3-(4-bromo-phenyl)-2-cyano-4-methylene-pentanedioic acid 1-ethyl ester 5-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-bromo-phenyl)-2-cyano-4-methylene-pentanedioic acid 1-ethyl ester 5-methyl ester

There total 1 articles about 3-(4-bromo-phenyl)-2-cyano-4-methylene-pentanedioic acid 1-ethyl ester 5-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: 82.0%

ethyl 2-cyanoacetate (105-56-6) + methyl 2-(acetoxy-(4-bromophenyl)methyl)acrylate (845866-13-9) → 3-(4-bromo-phenyl)-2-cyano-4-methylene-pentanedioic acid 1-ethyl ester 5-methyl ester (910641-57-5)

Guidance literature:

methyl 2-(acetoxy-(4-bromophenyl)methyl)acrylate; With 1,4-diaza-bicyclo[2.2.2]octane; In tetrahydrofuran; water; at 20 ℃; for 0.333333h;

ethyl 2-cyanoacetate; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2006.06.099

Reference yield: 58.0%

3-(4-bromo-phenyl)-2-cyano-4-methylene-pentanedioic acid 1-ethyl ester 5-methyl ester (910641-57-5) → 4-(4-bromo-phenyl)-5-methyl-6-oxo-piperidine-3-carboxylic acid ethyl ester (910641-90-6)

Guidance literature:

With hydrogen; nickel; In methanol; at 20 ℃; for 3h; under 2068.59 Torr;

DOI:10.1016/j.tet.2006.06.099

Reference yield:

3-(4-bromo-phenyl)-2-cyano-4-methylene-pentanedioic acid 1-ethyl ester 5-methyl ester (910641-57-5) → 6-(4-bromo-phenyl)-5-methyl-4-oxo-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / hydrogen; Raney nickel / methanol / 3 h / 20 °C / 2068.59 Torr

2: 60 percent / PCl₅; POCl₃ / 3 h / Heating

3: 58 percent / DBU / acetonitrile / 14 h / Heating

With phosphorus pentachloride; hydrogen; nickel; 1,8-diazabicyclo[5.4.0]undec-7-ene; trichlorophosphate; In methanol; acetonitrile;

DOI:10.1016/j.tet.2006.06.099

upstream raw materials:

ethyl 2-cyanoacetate

methyl 2-(acetoxy-(4-bromophenyl)methyl)acrylate

Downstream raw materials:

4-(4-bromo-phenyl)-5-methyl-6-oxo-piperidine-3-carboxylic acid ethyl ester

4-(4-bromo-phenyl)-5-chloro-5-methyl-6-oxo-piperidine-3-carboxylic acid ethyl ester