4-Chloro-3-(ethoxycarbonyl)phenylboronic acid

Base Information

• Chemical Name: 4-Chloro-3-(ethoxycarbonyl)phenylboronic acid
• CAS No.: 874219-46-2
• Molecular Formula: C9H10BClO4
• Molecular Weight: 228.44
• Hs Code.: 2931900090
• Mol file: 874219-46-2.mol

Synonyms:4-Chloro-3-(ethoxycarbonyl)phenylboronic acid;

Chemical Property of 4-Chloro-3-(ethoxycarbonyl)phenylboronic acid

Chemical Property:

• Vapor Pressure: 7.26E-07mmHg at 25°C
• Melting Point: 162-164 °C
• Refractive Index: 1.543
• Boiling Point: 392.5 °C at 760 mmHg
• Flash Point: 191.2 °C
• PSA: 66.76000
• Density: 1.33 g/cm³
• LogP: 0.19650
• Storage Temp.: Keep Cold

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Chloro-3-(ethoxycarbonyl)phenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Uses: suzuki reaction

Technology Process of 4-Chloro-3-(ethoxycarbonyl)phenylboronic acid

There total 2 articles about 4-Chloro-3-(ethoxycarbonyl)phenylboronic acid 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: 94.0%

ethyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (885067-50-5) → (4-chloro-3-(ethoxycarbonyl)phenyl)boronic acid (874219-46-2)

Guidance literature:

With sodium periodate; ammonium acetate; In water; acetone; at 20 ℃; for 19h;

DOI:10.1021/jo402526z

Reference yield:

5-Bromo-2-chloro-benzoic acid ethyl ester (76008-73-6) → (4-chloro-3-(ethoxycarbonyl)phenyl)boronic acid (874219-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 22 h / 80 °C / Inert atmosphere; Schlenk technique

2: ammonium acetate; sodium periodate / acetone; water / 19 h / 20 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; sodium periodate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ammonium acetate; potassium acetate; In 1,4-dioxane; water; acetone;

DOI:10.1021/jo402526z

Reference yield: 70.0%

(4-chloro-3-(ethoxycarbonyl)phenyl)boronic acid (874219-46-2) + 9-bromonoscapine (488721-01-3) → ethyl 2-chloro-5-((5R)-5-((1S)-4,5-dimethoxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-yl)benzoate

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; In ethanol; toluene; at 120 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.bmcl.2014.10.046

upstream raw materials:

5-Bromo-2-chloro-benzoic acid ethyl ester

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

Downstream raw materials:

tert-butyl 3-(4-chloro-3-(ethoxycarbonyl)phenyl)azetidine-1-carboxylate

Refernces