ethyl 4-(4-bromophenoxy)nicotinate

Base Information

• Chemical Name: ethyl 4-(4-bromophenoxy)nicotinate
• CAS No.: 1369628-08-9
• Molecular Formula: C₁₄H₁₂BrNO₃
• Molecular Weight: 322.158
• Mol file: 1369628-08-9.mol

Synonyms:ethyl 4-(4-bromophenoxy)nicotinate

Chemical Property of ethyl 4-(4-bromophenoxy)nicotinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-(4-bromophenoxy)nicotinate

There total 1 articles about ethyl 4-(4-bromophenoxy)nicotinate 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: 91.4%

4-bromo-phenol (106-41-2) + ethyl 4-chloronicotinate (37831-62-2) → ethyl 4-(4-bromophenoxy)nicotinate (1369628-08-9)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 20h;

Reference yield: 100.0%

ethyl 4-(4-bromophenoxy)nicotinate (1369628-08-9) → 4-(4-bromophenoxy)nicotinic acid (1369628-09-0)

Guidance literature:

ethyl 4-(4-bromophenoxy)nicotinate; With water; sodium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 7h;

With formic acid; In water; pH=~ 3; Cooling with ice;

Reference yield:

ethyl 4-(4-bromophenoxy)nicotinate (1369628-08-9) → rac-trans-(4a,10a)-2'-amino-8-(3-chloro-5-fluorophenyl)-1',2-dimethyl-1,2,3,4,4a,10a-hexahydrospiro[chromeno[3,2-c]pyridine-10,4'-imidazol]-5'(1'H)-one bis-trifluoroacetate

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium hydroxide; water / tetrahydrofuran / 7 h / 0 - 20 °C

1.2: pH ~ 3 / Cooling with ice

2.1: sulfuric acid / 16 h / 150 °C

2.2: 0 - 15 °C

3.1: 1,2-dichloro-ethane / 21 h / 80 °C / Capped tube

4.1: sodium tetrahydroborate / ethanol; tetrahydrofuran / 3 h / 0 °C

4.2: Cooling with ice

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane; tetrahydrofuran / 0.75 h / -78 °C

5.2: 1 h / -78 - 20 °C

6.1: potassium carbonate / methanol / 3 h / 20 °C / Resolution of cis/trans isomers

7.1: sodium hydrogensulfite; ammonium carbonate / ethanol / 23 h / 100 °C / bomb

8.1: potassium hydroxide; water / 1,4-dioxane / 96 h / 200 °C / Sealed bomb

8.2: 0 °C / pH ~ 7

9.1: tetrahydrofuran; hexanes; methanol / 19 h / 20 °C

10.1: triethylamine / tetrahydrofuran / 26 h / 60 °C

11.1: tert.-butylhydroperoxide; ammonia / water; tetrahydrofuran; methanol / 17 h / 20 - 35 °C / capped

12.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 15 h / 90 °C

With tert.-butylhydroperoxide; sodium tetrahydroborate; oxalyl dichloride; sulfuric acid; ammonia; water; ammonium carbonate; sodium carbonate; potassium carbonate; sodium hydrogensulfite; dimethyl sulfoxide; triethylamine; potassium hydroxide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; ethanol; dichloromethane; water; 1,2-dichloro-ethane;

upstream raw materials:

4-bromo-phenol

ethyl 4-chloronicotinate

Downstream raw materials:

4-(4-bromophenoxy)nicotinic acid

8-bromo-2-(4-methoxybenzyl)-10-oxo-10H-chromeno[3,2-c]pyridin-2-ium chloride

8-bromo-2-(4-methoxybenzyl)-2,3,4,4a,10,10a-hexahydro-1H-chromeno[3,2-c]pyridin-10-ol

rac-(4a)-8-bromo-2-(4-methoxybenzyl)-2,3,4,4a-tetrahydro-1H-chromeno[3,2-c]pyridin-10(10aH)-one

Refernces

• 1、 -. "HETEROCYCLIC INHIBITORS OF BETA - SECRETASE FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES". Page/Page column 65. . Retrieved 2012/06/15.