ethyl 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propanoate

Base Information

• Chemical Name: ethyl 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propanoate
• CAS No.: 1146546-99-7
• Molecular Formula: C₁₈H₂₇BO₅
• Molecular Weight: 334.22
• Mol file: 1146546-99-7.mol

Synonyms:ethyl 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propanoate

Chemical Property of ethyl 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propanoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propanoate

There total 5 articles about ethyl 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propanoate 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%

2-(4-bromophenoxy)-2-methylpropanoic acid ethyl ester (59227-80-4) + bis(pinacol)diborane (73183-34-3) → ethyl 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propanoate (1146546-99-7)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 100 ℃;

Reference yield: 87.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + tetrahydroxydiboron (13675-18-8) + Clofibrate (637-07-0) → ethyl 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propanoate (1146546-99-7)

Guidance literature:

tetrahydroxydiboron; Clofibrate; With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium acetate; XPhos; In ethanol; at 80 ℃; for 4h; Inert atmosphere; Schlenk technique;

2,3-dimethyl-2,3-butane diol; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201813708

Reference yield: 51.0%

Clofibrate (637-07-0) + bis(pinacol)diborane (73183-34-3) → ethyl 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propanoate (1146546-99-7)

Guidance literature:

With pyridine-4-carbonitrile; potassium phosphate; sodium oxalate; 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile; In acetonitrile; at 20 ℃; for 24h; Irradiation; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c05994

upstream raw materials:

2-(4-bromophenoxy)-2-methylpropanoic acid ethyl ester

bis(pinacol)diborane

4-bromo-phenol

ethyl 2-bromoisobutyrate

Downstream raw materials:

C₂₈H₂₉ClFNO₅

C₁₉H₂₂N₂O₅

C₂₈H₃₁NO₅

ethyl 2-methyl-2-(4-((trifluoromethyl)thio)phenoxy)propanoate

Refernces

• 1、 An, Rui,Li, Huimin,Liao, Lihao,Wu, Jin-Ji,Xu, Yang,Zhao, Xiaodan. "Catalytic Access to Functionalized Allylic gem-Difluorides via Fluorinative Meyer–Schuster-Like Rearrangement". supporting information. p. 11010 - 11019. Retrieved 2020/05/18.
• 2、 Dow, Robert L.,Ammirati, Mark,Bagley, Scott W.,Bhattacharya, Samit K.,Buckbinder, Leonard,Cortes, Christian,El-Kattan, Ayman F.,Ford, Kristen,Freeman, Gary B.,Guimar?es, Cristiano R. W.,Liu, Shenping,Niosi, Mark,Skoura, Athanasia,Tess, David. "2-Aminopyridine-Based Mitogen-Activated Protein Kinase Kinase Kinase Kinase 4 (MAP4K4) Inhibitors: Assessment of Mechanism-Based Safety". . p. 3114 - 3125. Retrieved 2018/04/23.