methyl 2-(4-bromophenyl)-2-diazoacetate

Base Information

• Chemical Name: methyl 2-(4-bromophenyl)-2-diazoacetate
• CAS No.: 264881-99-4
• Molecular Formula: C9H7BrN2O2
• Molecular Weight: 255.071
• Mol file: 264881-99-4.mol

Synonyms:methyl 2-(4-bromophenyl)-2-diazoacetate

Chemical Property of methyl 2-(4-bromophenyl)-2-diazoacetate

Chemical Property:

• Melting Point: 68 - 70 °C
• PSA: 63.69000
• LogP: 1.72206

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-(4-bromophenyl)-2-diazoacetate

There total 3 articles about methyl 2-(4-bromophenyl)-2-diazoacetate 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: 98.0%

(4-bromo-phenyl)-acetic acid methyl ester (41841-16-1) → methyl 2-(4-bromophenyl)-2-diazoacetate (264881-99-4)

Guidance literature:

With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2015.11.065

Reference yield: 98.0%

4-toluenesulfonyl azide (941-55-9) + (4-bromo-phenyl)-acetic acid methyl ester (41841-16-1) → methyl 2-(4-bromophenyl)-2-diazoacetate (264881-99-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 - 20 ℃;

DOI:10.1055/s-0034-1380426

Reference yield:

2-(4-bromophenyl)-acetic acid (1878-68-8) → methyl 2-(4-bromophenyl)-2-diazoacetate (264881-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: acetyl chloride / 0 - 20 °C / Inert atmosphere

2: 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4 h / 0 - 20 °C / Inert atmosphere

With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; In acetonitrile;

upstream raw materials:

(4-bromo-phenyl)-acetic acid methyl ester

2-(4-bromophenyl)-acetic acid

4-toluenesulfonyl azide

Downstream raw materials:

methyl (αR)-[(2S)-4-(triisopropylsilyloxy)-1,2-dihydro-naphthalen-2-yl]-(4-bromo-phenyl)acetate

Refernces

• 1、 Tayama, Eiji,Saito, Shun. "Regioselective synthesis of secondary 1,3-dienamides by successive eliminations". . p. 599 - 604. Retrieved 2016.
• 2、 Zhao, Yan-Rui,Li, Lei,Xu, Guo-Yong,Xuan, Jun. "All-Carbon Tetrasubstituted Olefins Synthesis from Diazo Compounds and Iodonium Ylides under Blue LED Irradiation". supporting information. p. 506 - 511. Retrieved 2021/12/08.
• 3、 Collins, Stuart G.,Lynch, Denis,Maguire, Anita R.,O'callaghan, Katie S.,O'mahony, Rosella M.. "Generation of Tosyl Azide in Continuous Flow Using an Azide Resin, and Telescoping with Diazo Transfer and Rhodium Acetate-Catalyzed O–H Insertion". . p. 2772 - 2785. Retrieved 2021/12/13.