2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 269410-15-3
• Molecular Formula: C18H20 B F O2
• Molecular Weight: 298.165
• Hs Code.: 2934999090
• Mol file: 269410-15-3.mol

Synonyms:2-Fluoro-4-biphenylboronic acid, pinacol ester;3-Fluoro-4-biphenylboronic acid, pinacol ester

Chemical Property of 2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• PSA: 18.46000
• LogP: 3.79190

Purity/Quality:

98% ^*data from raw suppliers

2-Fluoro-4-biphenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 3 articles about 2-(2-Fluorobiphenyl-4-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: 77.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (2-fluoro-[1,1'-biphenyl]-4-yl)boronic acid (178305-99-2) → 2-(2-fluoro-[1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (269410-15-3)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 12h; Molecular sieve;

DOI:10.1039/c8cc09523j

Reference yield:

1-bromo-3-fluoro-4-phenylbenzene (41604-19-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(2-fluoro-[1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (269410-15-3)

Guidance literature:

With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80 ℃; for 18h;

1-bromo-3-fluoro-4-phenylbenzene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In 1,4-dioxane; at 80 ℃; for 48h;

Reference yield:

2-fluorobiphenyl (321-60-8) + bis(pinacol)diborane (73183-34-3) → 2-(2-fluoro-[1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (269410-15-3) + C18H20BFO2

Guidance literature:

With trans-(^iPrPNP)Co(H)₂BPin; In tetrahydrofuran; at 50 ℃; for 24h; Overall yield = 62 %; Overall yield = 0.101 g; Inert atmosphere; Glovebox;

DOI:10.1021/jacs.6b13346

upstream raw materials:

1-bromo-3-fluoro-4-phenylbenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-fluorobiphenyl

bis(pinacol)diborane

Downstream raw materials:

3-[1-(4-chloro-benzyl)-5-(2-fluoro-biphenyl-4-yl)-3-methyl-1H-indol-2-yl]-2,2-dimethyl-propionic acid methyl ester

Refernces

• 1、 Obligacion, Jennifer V.,Bezdek, Máté J.,Chirik, Paul J.. "C(sp2)-H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic Opportunities". supporting information. p. 2825 - 2832. Retrieved 2017/03/08.