3-(benzyloxy)-5-bromopicolinic acid

Base Information

• Chemical Name: 3-(benzyloxy)-5-bromopicolinic acid
• CAS No.: 1393534-89-8
• Molecular Formula: C₁₃H₁₀BrNO₃
• Molecular Weight: 308.131
• Mol file: 1393534-89-8.mol

Synonyms:3-(benzyloxy)-5-bromopicolinic acid

Chemical Property of 3-(benzyloxy)-5-bromopicolinic acid

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(benzyloxy)-5-bromopicolinic acid

There total 4 articles about 3-(benzyloxy)-5-bromopicolinic acid 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: 91.0%

3-(benzyloxy)-5-bromopicolinonitrile (1393534-88-7) → 3-(benzyloxy)-5-bromopicolinic acid (1393534-89-8)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 84 ℃; for 4h;

Reference yield:

3,5-dibromo-2-cyanopyridine (61830-09-9) + benzyl alcohol (100-51-6,185532-71-2) → 3-(benzyloxy)-5-bromopicolinic acid (1393534-89-8) + 5-(benzyloxy)-3-bromopicolinic acid

Guidance literature:

benzyl alcohol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

3,5-dibromo-2-cyanopyridine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

With water; sodium hydroxide; Overall yield = 100 %; Overall yield = 5.13 g; Reflux;

Reference yield:

5-bromo-3-nitropyridine-2-carbonitrile (573675-25-9) → 3-(benzyloxy)-5-bromopicolinic acid (1393534-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0 - 35 °C

1.2: 1.33 h / 20 °C

2.1: water; sodium hydroxide / methanol / Reflux

With water; sodium hydride; sodium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1002/anie.201202000

upstream raw materials:

3-(benzyloxy)-5-bromopicolinonitrile

5-bromo-3-nitropyridine-2-carbonitrile

benzyl alcohol

3,5-dibromo-2-cyanopyridine

Downstream raw materials:

benzyl 2-(3-(benzyloxy)-5-(6-methoxynaphthalen-2-yl)picolinamido)acetate

benzyl 2-(3-(benzyloxy)-5-(naphthalen-2-yl)picolinamido)acetate

benzyl 2-(3-(benzyloxy)-5-(6-hydroxynaphthalen-2-yl)picolinamido)acetate

benzyl 2-(3-(benzyloxy)-5-bromopicolinamido)acetate