diethyl 2-(1R)-(3-(4-bromophenyl)-1-(4-chlorophenyl)-3-oxopropyl)malonate

Base Information

• Chemical Name: diethyl 2-(1R)-(3-(4-bromophenyl)-1-(4-chlorophenyl)-3-oxopropyl)malonate
• CAS No.: 1628735-85-2
• Molecular Formula: C₂₂H₂₂BrClO₅
• Molecular Weight: 481.771
• Mol file: 1628735-85-2.mol

Synonyms:diethyl 2-(1R)-(3-(4-bromophenyl)-1-(4-chlorophenyl)-3-oxopropyl)malonate

Chemical Property of diethyl 2-(1R)-(3-(4-bromophenyl)-1-(4-chlorophenyl)-3-oxopropyl)malonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl 2-(1R)-(3-(4-bromophenyl)-1-(4-chlorophenyl)-3-oxopropyl)malonate

There total 3 articles about diethyl 2-(1R)-(3-(4-bromophenyl)-1-(4-chlorophenyl)-3-oxopropyl)malonate 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: 92.0%

1-(4-bromophenyl)-3-(4-chlorophenyl)prop-2-en-1-one (6332-22-5) + diethyl malonate (105-53-3) → diethyl 2-(1R)-(3-(4-bromophenyl)-1-(4-chlorophenyl)-3-oxopropyl)malonate (1628735-85-2)

Guidance literature:

With C₉₃H₉₉N₆O₃⁽³⁺⁾*3Br^(1-); potassium carbonate; In water; toluene; at 20 ℃; for 1h; Reagent/catalyst; enantioselective reaction; Sonication;

DOI:10.1039/c4nj02395a

Reference yield: 90.0%

(E)-1-(4-bromophenyl)-3-(4-chlorophenyl)-prop-2-en-1-one (126443-16-1) + diethyl malonate (105-53-3) → diethyl 2-(1R)-(3-(4-bromophenyl)-1-(4-chlorophenyl)-3-oxopropyl)malonate (1628735-85-2)

Guidance literature:

With C₉₀H₉₆N₉O₃⁽³⁺⁾*3Br^(1-); potassium tert-butylate; In dichloromethane; for 4h; Reagent/catalyst; enantioselective reaction; Sonication;

DOI:10.1055/s-0033-1339124

Reference yield:

4-chlorobenzaldehyde (104-88-1) + para-bromoacetophenone (99-90-1) → diethyl 2-(1R)-(3-(4-bromophenyl)-1-(4-chlorophenyl)-3-oxopropyl)malonate (1628735-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / ethanol / 0.08 h

2: C₉₀H₉₆N₉O₃⁽³⁺⁾*3Br^(1-); potassium tert-butylate / dichloromethane / 4 h / Sonication

With C₉₀H₉₆N₉O₃⁽³⁺⁾*3Br^(1-); potassium tert-butylate; sodium hydroxide; In ethanol; dichloromethane; 2: |Michael Addition;

DOI:10.1055/s-0033-1339124

upstream raw materials:

4-chlorobenzaldehyde

para-bromoacetophenone

(E)-1-(4-bromophenyl)-3-(4-chlorophenyl)-prop-2-en-1-one

diethyl malonate

Refernces

• 1、 Kottala Vijaya, Ponmuthu,Murugesan, Sepperumal,Siva, Ayyanar. "Unexpected solvent/substitution-dependent inversion of the enantioselectivity in Michael addition reaction using chiral phase transfer catalysts". supporting information. p. 5209 - 5212. Retrieved 2015/08/19.