(Z)-4,4,5,5-tetramethyl-2-[2-(4-methoxyphenyl)-1-buten-1-yl]-1,3,2-dioxaborolane

Base Information

• Chemical Name: (Z)-4,4,5,5-tetramethyl-2-[2-(4-methoxyphenyl)-1-buten-1-yl]-1,3,2-dioxaborolane
• CAS No.: 958633-20-0
• Molecular Formula: C₁₇H₂₅BO₃
• Molecular Weight: 288.195
• Mol file: 958633-20-0.mol

Synonyms:(Z)-4,4,5,5-tetramethyl-2-[2-(4-methoxyphenyl)-1-buten-1-yl]-1,3,2-dioxaborolane

Chemical Property of (Z)-4,4,5,5-tetramethyl-2-[2-(4-methoxyphenyl)-1-buten-1-yl]-1,3,2-dioxaborolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-4,4,5,5-tetramethyl-2-[2-(4-methoxyphenyl)-1-buten-1-yl]-1,3,2-dioxaborolane

There total 6 articles about (Z)-4,4,5,5-tetramethyl-2-[2-(4-methoxyphenyl)-1-buten-1-yl]-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: 72.0%

2-[((4-methoxyphenyl)ethynyl)]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (872356-95-1) + ethene (74-85-1) → (Z)-4,4,5,5-tetramethyl-2-[2-(4-methoxyphenyl)-1-buten-1-yl]-1,3,2-dioxaborolane (958633-20-0)

Guidance literature:

ethene; With n-butyllithium; zirconocene dichloride; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

2-[((4-methoxyphenyl)ethynyl)]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; hexane; Further stages.;

DOI:10.1021/ja075234y

Reference yield: 72.0%

2-[((4-methoxyphenyl)ethynyl)]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (872356-95-1) + ethene (74-85-1) + water (7732-18-5) → (Z)-4,4,5,5-tetramethyl-2-[2-(4-methoxyphenyl)-1-buten-1-yl]-1,3,2-dioxaborolane (958633-20-0)

Guidance literature:

With n-butyllithium; zirconocene dichloride; In tetrahydrofuran; B compd. reacted with (C5H5)2ZrCl2/n-C4H9Li in THF at -78°C, reacted with C2H4; hydrolysed;

DOI:10.1021/ja075234y

Reference yield: 70.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + (Z)-1-(1-bromobut-1-en-2-yl)-4-methoxybenzene → (Z)-4,4,5,5-tetramethyl-2-[2-(4-methoxyphenyl)-1-buten-1-yl]-1,3,2-dioxaborolane (958633-20-0)

Guidance literature:

(Z)-1-(1-bromobut-1-en-2-yl)-4-methoxybenzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Schlenk technique; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at -78 - 20 ℃; for 10h; stereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/ejoc.201901119

upstream raw materials:

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

ethene

water

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