(R)-2-[1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: (R)-2-[1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1201898-93-2
• Molecular Formula: C₂₁H₂₆BClO₃
• Molecular Weight: 372.7
• Mol file: 1201898-93-2.mol

Synonyms:(R)-2-[1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of (R)-2-[1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 2 articles about (R)-2-[1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 87.0%

(S)-N,N-diisopropyl O-[1-(4-methoxyphenyl)]ethyl carbamate (1108740-07-3) + 4-chlorophenylboronic acid pinacol ester (195062-61-4) → (R)-2-[1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1201898-93-2)

Guidance literature:

(S)-N,N-diisopropyl O-[1-(4-methoxyphenyl)]ethyl carbamate; With N,N,N,N,-tetramethylethylenediamine; In diethyl ether; hexane; cyclohexane; at -75 - -70 ℃; for 0.416667h; Inert atmosphere;

4-chlorophenylboronic acid pinacol ester; In diethyl ether; hexane; cyclohexane; at -70 - 25 ℃; for 4.75h; Inert atmosphere;

DOI:10.1016/j.tet.2009.10.002

Reference yield:

1-(4-methoxyphenyl)ethyl N,N-diisopropylcarbamate + 4-chlorophenylboronic acid pinacol ester (195062-61-4) → (R)-2-[1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1201898-93-2)

Guidance literature:

With sec.-butyllithium; In diethyl ether; mixt. of (MeOC6H4)(CH3)CHOCb and sBuLi reacted at -78°C for 20 min, (ClC6H4)B(pinacol) added at -78°C, then heated to room. temp.;J. L. Stymiest et al., Nature 2008, 456, 778-782;

DOI:10.1002/anie.200901900

Reference yield: 71.0%

(R)-2-[1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1201898-93-2) + 4-cyanobenzaldehyde (105-07-7) → 4-((2S)-2-(4-chlorophenyl)-1-hydroxy-2-(4-methoxyphenyl)propyl)benzonitrile (1190868-74-6)

Guidance literature:

(R)-2-[1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; With potassium hydrogenfluoride; In methanol; Inert atmosphere;

4-cyanobenzaldehyde; With chloro(1,5-cyclooctadiene)rhodium(I) dimer; water; In 1,4-dioxane; at 60 ℃; for 24h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.200901900

upstream raw materials:

(S)-N,N-diisopropyl O-[1-(4-methoxyphenyl)]ethyl carbamate

4-chlorophenylboronic acid pinacol ester

Downstream raw materials:

4-((2S)-2-(4-chlorophenyl)-1-hydroxy-2-(4-methoxyphenyl)propyl)benzonitrile

potassium (Me)(p-ClC₆H₄)(p-MeOC₆H₄)C(trifluoroborate)

(S)-1-(4-chlorophenyl)-1-(4-methoxyphenyl)ethanol

Refernces

• 1、 Ros, Abel,Aggarwal, Varinder K.. "Complete stereoretention in the rhodium-catalyzed 1,2-addition of chiral secondary and tertiary alkyl potassium trifluoroborate salts to aldehydes". scheme or table. p. 6289 - 6292. Retrieved 2009/12/06.