Methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Base Information

• Chemical Name: Methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 1016979-31-9
• Molecular Formula: C14H18BFO4
• Molecular Weight: 280.104
• Hs Code.: 2934999090
• Mol file: 1016979-31-9.mol

Synonyms:3-Fluoro-5-methoxycarbonylphenylboronic acid, pinacol ester;Methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;3-Fluoro-5-(Methoxycarbonyl)benzeneboronic acid pinacol ester, 96%;3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester

Chemical Property of Methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Chemical Property:

• Boiling Point: 373.3±37.0 °C(Predicted)
• PSA: 44.76000
• Density: 1.14±0.1 g/cm3(Predicted)
• LogP: 1.91150
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

3-Fluoro-5-methoxycarbonylphenylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Fluoro-5-methoxycarbonylphenylboronic acid, pinacol ester

Technology Process of Methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

There total 5 articles about Methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 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: 81.0%

methyl 3-bromo-5-fluoro-benzoate (334792-52-8) + bis(pinacol)diborane (73183-34-3) → methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1016979-31-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 5,5-dimethyl-1,3-cyclohexadiene; at 90 ℃; for 8h;

DOI:10.1134/S0022476621060044

Reference yield:

methyl 3-fluorobenzoate (455-68-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1016979-31-9) + methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (603122-79-8)

Guidance literature:

With 1,2,3-trimethoxybenzene; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; In 2-methyltetrahydrofuran; at 80 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jacs.1c00523

Reference yield:

3-bromo-5-fluorobenzoic acid (176548-70-2) → methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1016979-31-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0.5 h / Cooling with ice

2: dichloromethane / 0.33 h / Cooling with ice

3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 5,5-dimethyl-1,3-cyclohexadiene / 8 h / 90 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; oxalyl dichloride; potassium acetate; N,N-dimethyl-formamide; In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane;

DOI:10.1134/S0022476621060044

upstream raw materials:

methyl 3-fluorobenzoate

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

3-bromo-5-fluorobenzoic acid

3-bromo-5-fluoro-benzoyl chloride

Downstream raw materials:

methyl 3-fluorobenzoate

methyl 3-fluoro-5-hydroxybenzoate