2-Fluoro-3-(trifluoromethyl)phenylboronic acid pinacol ester

Base Information

• Chemical Name: 2-Fluoro-3-(trifluoromethyl)phenylboronic acid pinacol ester
• CAS No.: 627526-48-1
• Molecular Formula: C₁₃H₁₅BF₄O₂
• Molecular Weight: 290.066
• Mol file: 627526-48-1.mol

Synonyms:

Chemical Property of 2-Fluoro-3-(trifluoromethyl)phenylboronic acid pinacol ester

Chemical Property:

• Boiling Point: 303.5±42.0 °C(Predicted)
• Density: 1.20±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

2-(2-Fluoro-3-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Fluoro-3-(trifluoromethyl)phenylboronic acid pinacol ester

There total 10 articles about 2-Fluoro-3-(trifluoromethyl)phenylboronic acid pinacol ester 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: 79.0%

C13H14BBrF4O2 → 2-(2-fluoro-3-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (627526-48-1)

Guidance literature:

With potassium fluoride; palladium diacetate; In tetrahydrofuran; water; at 20 ℃; for 4h; Reagent/catalyst; chemoselective reaction; Catalytic behavior; Inert atmosphere;

DOI:10.1021/ol5028738

Reference yield:

C13H14BBrF4O2 → 2-(2-fluoro-3-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (627526-48-1) + 1-fluoro-2-trifluoromethylbenzene (392-85-8)

Guidance literature:

With palladium on activated carbon; ammonium formate; In methanol; at 60 ℃; for 0.666667h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol5028738

Reference yield:

5-bromo-2-fluorobenzotrifluoride (393-37-3) → 2-(2-fluoro-3-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (627526-48-1) + 1-fluoro-2-trifluoromethylbenzene (392-85-8)

Guidance literature:

Multi-step reaction with 2 steps

1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere; Glovebox

2: palladium on activated carbon; ammonium formate / methanol / 0.67 h / 60 °C / Inert atmosphere; Schlenk technique

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; palladium on activated carbon; ammonium formate; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; methanol;

DOI:10.1021/ol5028738

upstream raw materials:

5-bromo-2-fluorobenzotrifluoride

bis(pinacol)diborane

1-fluoro-2-trifluoromethylbenzene

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

Refernces

• 1、 Pabst, Tyler P.,Obligacion, Jennifer V.,Rochette, étienne,Pappas, Iraklis,Chirik, Paul J.. "Cobalt-Catalyzed Borylation of Fluorinated Arenes: Thermodynamic Control of C(sp2)-H Oxidative Addition Results in ortho-to-Fluorine Selectivity". supporting information. p. 15378 - 15389. Retrieved 2019/11/02.
• 2、 -. "METHODS FOR PRODUCING BORYLATED ARENES". Paragraph 0336; 0339; 0340; 0343. . Retrieved 2015/03/16.