4-(Benzyloxy)-2-chloro-3-(trifluoromethyl)pyridine

Base Information

• Chemical Name: 4-(Benzyloxy)-2-chloro-3-(trifluoromethyl)pyridine
• CAS No.: 1254981-27-5
• Molecular Formula: C13H9ClF3NO
• Molecular Weight: 287.669
• Mol file: 1254981-27-5.mol

Synonyms:4-benzyloxy-2-chloro-3-trifluoromethyl-pyridine;4-benzyloxy-3-trifluoromethyl-2-chloro-pyridine;

Chemical Property of 4-(Benzyloxy)-2-chloro-3-(trifluoromethyl)pyridine

Chemical Property:

• PSA: 22.12000
• LogP: 4.33280
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

4-(benzyloxy)-2-chloro-3-(trifluoromethyl)pyridine 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-(Benzyloxy)-2-chloro-3-(trifluoromethyl)pyridine

There total 4 articles about 4-(Benzyloxy)-2-chloro-3-(trifluoromethyl)pyridine 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: 72.0%

→ 4-(benzyloxy)-2-chloro-3-(trifluoromethyl)pyridine (1254981-27-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h;

In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 1h;

Reference yield: 50.0%

2,4-dichloro-3-(trifluoromethyl)pyridine (1186194-98-8) + benzyl alcohol (100-51-6,185532-71-2) → 4-(benzyloxy)-2-chloro-3-(trifluoromethyl)pyridine (1254981-27-5)

Guidance literature:

benzyl alcohol; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

2,4-dichloro-3-(trifluoromethyl)pyridine; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 1h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.bmc.2016.11.018

Reference yield:

2,4-dichloropyridine (26452-80-2) → 4-(benzyloxy)-2-chloro-3-(trifluoromethyl)pyridine (1254981-27-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: copper(l) iodide; 2,2-difluoro-2-(fluorosulfonyl)acetate / N,N-dimethyl-formamide / 5 h / 100 °C / Sealed tube

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.03 h / 0 °C

3.2: 0 - 20 °C

With copper(l) iodide; n-butyllithium; 2,2-difluoro-2-(fluorosulfonyl)acetate; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

2,4-dichloro-3-(trifluoromethyl)pyridine

benzyl alcohol

2,4-dichloropyridine

2,4-dichloro-3-iodo-pyridine

Downstream raw materials:

4-(benzyloxy)-2-hydrazineyl-3-(trifluoromethyl)pyridine

N'-[4-(benzyloxy)-3-(trifluoromethyl)pyridin-2-yl]-2-cyclopropylacetohydrazide

3-(cyclopropylmethyl)-7-[4-(3,6-difluoro-2-methoxyphenyl)-1-piperidinyl]-8-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyridine

3-(cyclopropylmethyl)-7-[4-(2,4-difluorophenyl)-1-piperidinyl]-8-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyridine

Refernces

• 1、 Higgins, Mendi A.,Marcin, Lawrence R.,Christopher Zusi,Gentles, Robert,Ding, Min,Pearce, Bradley C.,Easton, Amy,Kostich, Walter A.,Seager, Matthew A.,Bourin, Clotilde,Bristow, Linda J.,Johnson, Kim A.,Miller, Regina,Hogan, John,Whiterock, Valerie,Gulianello, Michael,Ferrante, Meredith,Huang, Yanling,Hendricson, Adam,Alt, Andrew,Macor, John E.,Bronson, Joanne J.. "Triazolopyridine ethers as potent, orally active mGlu2positive allosteric modulators for treating schizophrenia". . p. 496 - 513. Retrieved 2016/12/30.
• 2、 -. "1,2,4-TRIAZOLO[4,3-a]PYRIDINE COMPOUNDS AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS". Page/Page column 33. . Retrieved 2015/03/28.