4-Chloro-3-fluorophenylboronic acid pinacol ester

Base Information

• Chemical Name: 4-Chloro-3-fluorophenylboronic acid pinacol ester
• CAS No.: 627525-83-1
• Molecular Formula: C₁₂H₁₅BClFO₂
• Molecular Weight: 256.512
• Mol file: 627525-83-1.mol

Synonyms:

Chemical Property of 4-Chloro-3-fluorophenylboronic acid pinacol ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

2-(4-Chloro-3-Fluorophenyl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Chloro-3-fluorophenylboronic acid pinacol ester

There total 5 articles about 4-Chloro-3-fluorophenylboronic 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: 59.0%

2-chloro-5-bromofluorobenzene (60811-18-9) + bis(pinacol)diborane (73183-34-3) → 2-(4-chloro-3-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (627525-83-1)

Guidance literature:

With potassium acetate; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; for 12.5h; Heating / reflux;

Reference yield:

1-chloro-2-fluorobenzene (348-51-6) + bis(pinacol)diborane (73183-34-3) → 2-(3-chloro-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (635305-46-3) + 2-(4-chloro-3-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (627525-83-1) + 2-(3-chloro-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1192025-01-6)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,4-dioxane; at 50 ℃; for 15h; Overall yield = 62 percentSpectr.; regioselective reaction;

DOI:10.1021/acscatal.1c01206

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + 1-chloro-2-fluorobenzene (348-51-6) + C5H3BCl4N(1+)*AlCl4(1-) → 2-(3-chloro-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (635305-46-3) + 2-(4-chloro-3-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (627525-83-1)

Guidance literature:

1-chloro-2-fluorobenzene; C₅H₃BCl₄N⁽¹⁺⁾*AlCl₄^(1-); With aluminum (III) chloride; In dimethylsulfoxide-d6; at 140 ℃; for 41h; Glovebox; Sealed tube;

2,3-dimethyl-2,3-butane diol; With triethylamine; In dimethylsulfoxide-d6; dichloromethane; at 0 - 20 ℃; for 14h; Overall yield = 74 %; Overall yield = 152 mg; Inert atmosphere;

DOI:10.1039/c4cc10153g

upstream raw materials:

2-chloro-5-bromofluorobenzene

bis(pinacol)diborane

2,3-dimethyl-2,3-butane diol

1-chloro-2-fluorobenzene

Refernces

• 1、 Del Grosso, Alessandro,Ayuso Carrillo, Josue,Ingleson, Michael J.. "Regioselective electrophilic borylation of haloarenes". supporting information. p. 2878 - 2881. Retrieved 2015/02/19.
• 2、 -. "ISOXAZOL-3(2H)-ONE ANALOGS AS THERAPEUTIC AGENTS". Page/Page column 24-25. . Retrieved 2010/11/03.