(E)-2-(3,3-dimethyl-1-(p-tolyl)but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: (E)-2-(3,3-dimethyl-1-(p-tolyl)but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1391743-04-6
• Molecular Formula: C₁₉H₂₉BO₂
• Molecular Weight: 300.249
• Mol file: 1391743-04-6.mol

Synonyms:(E)-2-(3,3-dimethyl-1-(p-tolyl)but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of (E)-2-(3,3-dimethyl-1-(p-tolyl)but-1-en-2-yl)-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 (E)-2-(3,3-dimethyl-1-(p-tolyl)but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 2 articles about (E)-2-(3,3-dimethyl-1-(p-tolyl)but-1-en-2-yl)-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: 66.0%

para-bromotoluene (106-38-7) + (E)-2,2'-(3,3-dimethylbut-1-ene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (815575-36-1) → (E)-2-(3,3-dimethyl-1-(p-tolyl)but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1391743-04-6)

Guidance literature:

With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; water; at 80 ℃; for 16h;

DOI:10.1002/chem.201200246

Reference yield:

3,3-Dimethylbut-1-yne (917-92-0) → (E)-2-(3,3-dimethyl-1-(p-tolyl)but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1391743-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 20 h / 80 °C

2: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran; water / 16 h / 80 °C

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; water; N,N-dimethyl-formamide; 2: Suzuki-Miyaura coupling;

DOI:10.1002/chem.201200246

Reference yield:

(E)-2-(3,3-dimethyl-1-(p-tolyl)but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1391743-04-6) → (-)-2-(3,3-dimethyl-1-(p-tolyl)butan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Guidance literature:

With C₃₀H₄₂IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; In dichloromethane; at 20 ℃; for 12h; under 37503.8 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1002/chem.201200246

upstream raw materials:

3,3-Dimethylbut-1-yne

para-bromotoluene

(E)-2,2'-(3,3-dimethylbut-1-ene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)