rac-N-(2-(5-bromo-2-fluorophenyl)-1-hydroxypropan-2-yl)-2-chloroacetamide

Base Information

• Chemical Name: rac-N-(2-(5-bromo-2-fluorophenyl)-1-hydroxypropan-2-yl)-2-chloroacetamide
• CAS No.: 1266784-29-5
• Molecular Formula: C₁₁H₁₂BrClFNO₂
• Molecular Weight: 324.577
• Mol file: 1266784-29-5.mol

Synonyms:rac-N-(2-(5-bromo-2-fluorophenyl)-1-hydroxypropan-2-yl)-2-chloroacetamide

Chemical Property of rac-N-(2-(5-bromo-2-fluorophenyl)-1-hydroxypropan-2-yl)-2-chloroacetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-N-(2-(5-bromo-2-fluorophenyl)-1-hydroxypropan-2-yl)-2-chloroacetamide

There total 9 articles about rac-N-(2-(5-bromo-2-fluorophenyl)-1-hydroxypropan-2-yl)-2-chloroacetamide 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: 60.0%

→ rac-N-(2-(5-bromo-2-fluorophenyl)-1-hydroxypropan-2-yl)-2-chloroacetamide (1266784-29-5)

Guidance literature:

Reference yield: 38.0%

(RS)-2-amino-2-(5-bromo-2-fluoro-phenyl)-propan-1-ol (1266784-24-0) + chloroacetyl chloride (79-04-9) → rac-N-(2-(5-bromo-2-fluorophenyl)-1-hydroxypropan-2-yl)-2-chloroacetamide (1266784-29-5)

Guidance literature:

With sodium carbonate; In dichloromethane; water; at 0 - 25 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.0c02143

Reference yield:

5-bromo-2-fluoro-benzoic acid (146328-85-0) → rac-N-(2-(5-bromo-2-fluorophenyl)-1-hydroxypropan-2-yl)-2-chloroacetamide (1266784-29-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: dmap; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 0 - 20 °C

2.1: tetrahydrofuran / 0.33 h / 12 - 16 °C / Reflux

2.2: Cooling

3.1: ethanol / 16 h / 120 °C / autoclave

4.1: sodium hydroxide; water

5.1: thionyl chloride

6.1: lithium aluminium tetrahydride / tetrahydrofuran

7.1: acetonitrile

With dmap; lithium aluminium tetrahydride; thionyl chloride; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

upstream raw materials:

(RS)-2-amino-2-(5-bromo-2-fluoro-phenyl)-propan-1-ol

chloroacetyl chloride

rac-2-amino-2-(5-bromo-2-fluoro-phenyl)-propionic acid methyl ester

5-bromo-2-fluoro-benzoic acid

Downstream raw materials:

rac-5-(5-bromo-2-fluorophenyl)-5-methylmorpholin-3-one

(RS)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-methyl-morpholin-3-one

(R)-(+)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide

(S)-(-)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide