METHYL 2-BROMOMETHYL-5-FLUORO-BENZOATE

Base Information

• Chemical Name: METHYL 2-BROMOMETHYL-5-FLUORO-BENZOATE
• CAS No.: 138786-65-9
• Molecular Formula: C9H8BrFO2
• Molecular Weight: 247.064
• Hs Code.: 2916399090
• Mol file: 138786-65-9.mol

Synonyms:METHYL 2-BROMOMETHYL-5-FLUORO-BENZOATE

Chemical Property of METHYL 2-BROMOMETHYL-5-FLUORO-BENZOATE

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.542
• Boiling Point: 306.091°C at 760 mmHg
• Flash Point: 138.919°C
• PSA: 26.30000
• Density: 1.534g/cm³
• LogP: 2.50720
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99.3% ^*data from raw suppliers

Methyl 2-(bromomethyl)-5-fluorobenzoate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 2-(bromomethyl)-5-fluorobenzoate is used as a reactant in the preparation of isoindolones as metabotropic glutamate receptor potentiators.

Technology Process of METHYL 2-BROMOMETHYL-5-FLUORO-BENZOATE

There total 3 articles about METHYL 2-BROMOMETHYL-5-FLUORO-BENZOATE 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: 99.0%

5-fluoro-2-methylbenzoic acid methyl ester (175278-29-2) → methyl 2-(bromomethyl)-5-fluorobenzoate (138786-65-9)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 80 ℃; for 4h;

DOI:10.1016/j.bmcl.2010.06.134

Reference yield:

5-fluoro-2-methylbenzoic acid (33184-16-6) → methyl 2-(bromomethyl)-5-fluorobenzoate (138786-65-9)

Guidance literature:

Multi-step reaction with 2 steps

1: conc. H₂SO₄ / 24 h / Heating

2: N-bromosuccinimide, benzoyl peroxide / CCl₄ / 3 h / Heating

With N-Bromosuccinimide; Perbenzoic acid; sulfuric acid; In tetrachloromethane;

DOI:10.1021/jm00085a005

Reference yield:

methanol (67-56-1) + 5-fluoro-2-methylbenzoic acid (33184-16-6) → methyl 2-(bromomethyl)-5-fluorobenzoate (138786-65-9)

Guidance literature:

methanol; 5-fluoro-2-methylbenzoic acid; With sulfuryl dichloride; for 8h; Reflux;

With N-Bromosuccinimide; dibenzoyl peroxide; In 1,2-dichloro-ethane; for 8h; Reflux;

DOI:10.1002/anie.202113464

upstream raw materials:

5-fluoro-2-methylbenzoic acid methyl ester

5-fluoro-2-methylbenzoic acid

methanol

Downstream raw materials:

2-(5-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-tetrazol-2-ylmethyl)-5-fluoro-benzoic acid

2-(4-bromophenyl)-6-fluoro-2,3-dihydro-1H-isoindol-1-one

6-fluoro-2-(4-dimethylaminophenyl)-2,3-dihydroisoindol-1-one

methyl 2-[(4-{[4-(2,4-dichlorophenoxy)piperidin-1-yl]methyl}piperidin-1-yl)methyl]-5-fluorobenzoate

Refernces

• 1、 Li, Qing,Meng, Liuwei,Zhou, Siru,Deng, Xiaoyan,Wang, Na,Ji, Yi,Peng, Yichun,Xing, Junhao,Yao, Gongmei. "Rapid generation of novel benzoic acid–based xanthine derivatives as highly potent, selective and long acting DPP-4 inhibitors: Scaffold-hopping and prodrug study". . p. 509 - 523. Retrieved 2019.
• 2、 Chen, Peng-Fei,Wang, Binju,Wu, Peng,Ye, Long-Wu,Zhou, Bo. "Br?nsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo- and Enantioselective Synthesis of Spirolactams". supporting information. p. 27164 - 27170. Retrieved 2021/11/22.
• 3、 -. "Influenza virus replication inhibitor and uses thereof". Paragraph 0530; 0532-0534. . Retrieved 2020/05/05.