2-Bromo-5-methoxyphenylboronic acid pinacol ester

Base Information

• Chemical Name: 2-Bromo-5-methoxyphenylboronic acid pinacol ester
• CAS No.: 1256781-58-4
• Molecular Formula: C₁₃H₁₈BBrO₃
• Molecular Weight: 312.999
• Hs Code.: 2931900090
• Mol file: 1256781-58-4.mol

Synonyms:2-(2-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-Bromo-5-methoxyphenylboronic acid pinacol ester

Chemical Property:

• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

2-(2-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Bromo-5-methoxyphenylboronic acid pinacol ester

There total 3 articles about 2-Bromo-5-methoxyphenylboronic 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: 93.0%

3-methoxyphenylboronic acid pinacol ester (325142-84-5) → 2-(2-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1256781-58-4)

Guidance literature:

With gold(III) chloride; N-Bromosuccinimide; In 1,2-dichloro-ethane; at 20 ℃; for 6h; regioselective reaction;

DOI:10.1021/ol102350v

Reference yield: 87.0%

N-Bromosuccinimide (128-08-5) + 3-methoxyphenylboronic acid pinacol ester (325142-84-5) → 2-(2-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1256781-58-4)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 14h; Reagent/catalyst;

DOI:10.1016/j.tetlet.2014.06.003

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + (2-bromo-5-methoxyphenyl)boronic acid (89694-44-0) → 2-(2-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1256781-58-4)

Guidance literature:

In diethyl ether; at 20 ℃; for 15h;

DOI:10.1021/ol5006246

upstream raw materials:

3-methoxyphenylboronic acid pinacol ester

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

(2-bromo-5-methoxyphenyl)boronic acid

N-Bromosuccinimide

Refernces

• 1、 Garcia-Lopez, Jose-Antonio,Greaney, Michael F.. "Use of 2-bromophenylboronic esters as benzyne precursors in the Pd-catalyzed synthesis of triphenylenes". supporting information. p. 2338 - 2341. Retrieved 2014/05/20.
• 2、 Qiu, Di,Mo, Fanyang,Zheng, Zhitong,Zhang, Yan,Wang, Jianbo. "Gold(iii)-catalyzed halogenation of aromatic boronates with N -halosuccinimides". supporting information; experimental part. p. 5474 - 5477. Retrieved 2011/02/22.