methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Base Information

• Chemical Name: methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 625470-33-9
• Molecular Formula: C14H18BClO4
• Molecular Weight: 296.559
• Mol file: 625470-33-9.mol

Synonyms:methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

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

Chemical Property:

• Boiling Point: 387.6±32.0 °C(Predicted)
• PSA: 44.76000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 2.42580

Purity/Quality:

97% ^*data from raw suppliers

4-Chloro-(3-methoxycarbonyl)phenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 2 articles about methyl 2-chloro-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: 60.0%

bis(pinacol)diborane (73183-34-3) + methyl 5-bromo-2-chloro-benzoate (251085-87-7) → methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (625470-33-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; Heating;

DOI:10.1016/j.bmcl.2011.06.117

Reference yield:

5-bromo-2-chlorobenzoic acid (21739-92-4) → methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (625470-33-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / water

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / Heating

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.06.117

Reference yield:

2-chloro-5-methylpyridine (18368-64-4) + methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (625470-33-9) → 2-chloro-5-(6-methyl-pyridin-3-yl)-benzoic acid methyl ester (792911-89-8)

Guidance literature:

With caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 20 - 80 ℃; for 25h; molecular sieves;

upstream raw materials:

5-bromo-2-chlorobenzoic acid

bis(pinacol)diborane

methyl 5-bromo-2-chloro-benzoate

Downstream raw materials:

2-chloro-5-(6-methyl-pyridin-3-yl)-benzoic acid methyl ester

C₂₁H₂₅ClN₂O₂

C₁₈H₂₁ClN₂O₃

C₁₃H₁₀ClNO₂