(S)-2-(1-chloro-2-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: (S)-2-(1-chloro-2-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1360649-43-9
• Molecular Formula: C₁₅H₂₂BClO₃
• Molecular Weight: 296.602
• Mol file: 1360649-43-9.mol

Synonyms:(S)-2-(1-chloro-2-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of (S)-2-(1-chloro-2-(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 (S)-2-(1-chloro-2-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 5 articles about (S)-2-(1-chloro-2-(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: 9.0%

2-(1-chloro-2-(4-methoxyphenyl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1360649-18-8) → (S)-2-(1-chloro-2-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1360649-43-9) + (R)-2-(1-chloro-2-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane + 2-[2-(4-methoxy-phenyl)-ethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Guidance literature:

With (η-1,5-cyclooctadiene) {[4(R),5(R)]-1-benzoyl-2-[(S)-2-diphenylphosphinoferrocenyl]-4,5-diphenyl-4,5-dihydro-1-imidazole} iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen; In dichloromethane; at 50 ℃; for 18h; under 22502.3 Torr; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/anie.201106262

Reference yield:

dichloromethane (75-09-2) + 2-[(4-methoxyphenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (475250-52-3) → (S)-2-(1-chloro-2-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1360649-43-9)

Guidance literature:

dichloromethane; 2-[(4-methoxyphenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; With lithium diisopropyl amide; In diethyl ether; at -78 ℃; for 0.25h;

With C₃₄H₄₂BClF₆N₃O₃S^(1-)*Li⁽¹⁺⁾; In diethyl ether; at -35 ℃; for 20h; enantioselective reaction;

DOI:10.1126/science.abm0386

Reference yield:

2-[((4-methoxyphenyl)ethynyl)]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (872356-95-1) → (S)-2-(1-chloro-2-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1360649-43-9) + (R)-2-(1-chloro-2-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane + 2-[2-(4-methoxy-phenyl)-ethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Guidance literature:

Multi-step reaction with 2 steps

1.1: Schwartz's reagent / dichloromethane / 1 h / 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: (η-1,5-cyclooctadiene) {[4(R),5(R)]-1-benzoyl-2-[(S)-2-diphenylphosphinoferrocenyl]-4,5-diphenyl-4,5-dihydro-1-imidazole} iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen / dichloromethane / 18 h / 50 °C / 22502.3 Torr

With Schwartz's reagent; (η-1,5-cyclooctadiene) {[4(R),5(R)]-1-benzoyl-2-[(S)-2-diphenylphosphinoferrocenyl]-4,5-diphenyl-4,5-dihydro-1-imidazole} iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen; In dichloromethane;

DOI:10.1002/anie.201106262

upstream raw materials:

2-[((4-methoxyphenyl)ethynyl)]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

2-(1-chloro-2-(4-methoxyphenyl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-methoxyphenylacetylen