2-[4-(bromomethyl)phenyl]-5-fluoropyridine

Base Information

• Chemical Name: 2-[4-(bromomethyl)phenyl]-5-fluoropyridine
• CAS No.: 1257426-56-4
• Molecular Formula: C₁₂H₉BrFN
• Molecular Weight: 266.113
• Mol file: 1257426-56-4.mol

Synonyms:2-[4-(bromomethyl)phenyl]-5-fluoropyridine

Chemical Property of 2-[4-(bromomethyl)phenyl]-5-fluoropyridine

Chemical Property:

Purity/Quality:

2-[4-(Bromomethyl)phenyl]-5-fluoropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2-[4-(Bromomethyl)phenyl]-5-fluoropyridine is an intermediate used for the synthesis of diazabiphenyl analogues for antitubercular therapy.

Technology Process of 2-[4-(bromomethyl)phenyl]-5-fluoropyridine

There total 5 articles about 2-[4-(bromomethyl)phenyl]-5-fluoropyridine 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: 87.0%

[4-(5-fluoro-2-pyridinyl)phenyl]methanol (1257426-54-2) → 2-[4-(bromomethyl)phenyl]-5-fluoropyridine (1257426-56-4)

Guidance literature:

With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 20 ℃; for 3h;

Reference yield: 65.0%

5-fluoro-2-(4-methylphenyl)pyridine (1198348-26-3) → 2-[4-(bromomethyl)phenyl]-5-fluoropyridine (1257426-56-4)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 16h; Inert atmosphere; Reflux;

DOI:10.1021/acs.jmedchem.5b01200

Reference yield:

2-bromo-5-fluoropyridine (41404-58-4) → 2-[4-(bromomethyl)phenyl]-5-fluoropyridine (1257426-56-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; ethanol; water / 3.33 h / 89 °C / Inert atmosphere

2: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 3 h / 20 °C

With N-Bromosuccinimide; sodium carbonate; triphenylphosphine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; dichloromethane; water; toluene;

upstream raw materials:

[4-(5-fluoro-2-pyridinyl)phenyl]methanol

p-hydroxymethylphenylboronic acid

2-bromo-5-fluoropyridine

4-methylphenylboronic acid

Downstream raw materials:

(6S)-6-{[4-(5-fluoro-2-pyridinyl)benzyl]oxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Refernces

• 1、 -. "NITROIMIDAZOOXAZINES AND THEIR USES IN ANTI-TUBERCULAR THERAPY". Page/Page column 21. . Retrieved 2012/02/06.
• 2、 Kmentova, Iveta,Sutherland, Hamish S.,Palmer, Brian D.,Blaser, Adrian,Franzblau, Scott G.,Wan, Baojie,Wang, Yuehong,Ma, Zhenkun,Denny, William A.,Thompson, Andrew M.. "Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6 S)-2-nitro-6-{[4-(trifluoromethoxy) benzyl]oxy}-6,7-dihydro-5 H-imidazo[2,1-b][1,3]oxazine (PA-824)". experimental part. p. 8421 - 8439. Retrieved 2011/02/21.