3-(2'-pyridylthio)phenylboronic acid

Base Information

• Chemical Name: 3-(2'-pyridylthio)phenylboronic acid
• CAS No.: 1258271-19-0
• Molecular Formula: C₁₁H₁₀BNO₂S
• Molecular Weight: 231.083
• Mol file: 1258271-19-0.mol

Synonyms:3-(2'-pyridylthio)phenylboronic acid

Chemical Property of 3-(2'-pyridylthio)phenylboronic acid

Chemical Property:

Purity/Quality:

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Technology Process of 3-(2'-pyridylthio)phenylboronic acid

There total 2 articles about 3-(2'-pyridylthio)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: 65.0%

Trimethyl borate (121-43-7,63156-11-6) + (3-bromophenyl)(phenyl)sulfane (52089-10-8) → 3-(2'-pyridylthio)phenylboronic acid (1258271-19-0)

Guidance literature:

(3-bromophenyl)(phenyl)sulfane; With n-butyllithium; In diethyl ether; hexane; at -90 - -40 ℃; Inert atmosphere;

Trimethyl borate; In diethyl ether; hexane; at -80 - 20 ℃; Inert atmosphere;

With hydrogenchloride; water; In diethyl ether; hexane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1246/bcsj.20100076

Reference yield: 65.0%

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-3-(2'-pyridylthio)benzene (1258271-18-9) + water (7732-18-5) → 3-(2'-pyridylthio)phenylboronic acid (1258271-19-0)

Guidance literature:

With n-BuLi; HCl; In diethyl ether; hexane; bromide was dissolved in Et2O under Ar; cooled to -90°C (liq. N2/methanol bath); soln. of BuLi in hexane was added dropwise; warmed to -40°C for 40 min; B compd. was added at -80°C; warmed to room temp.; stirred for 10 h; aq. HCl added at 0°C; stirred at room temp. for 2 h; K2CO3 added to aq. layer; extd. (Et2O); org. layer combined; washed (H2O); dried (Na2SO4); filtered; concd.; dissolved in CHCl3; filtered; washed (CHCl3); dried (vac.); elem. anal.;

DOI:10.1246/bcsj.20100076

Reference yield: 85.0%

2-bromo-pyridine (109-04-6) + 3-(2'-pyridylthio)phenylboronic acid (1258271-19-0) → 1-(2'-pyridyl)-3-(2'-pyridylthio)benzene (1258271-17-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; potassium carbonate; In 1,2-dimethoxyethane; for 6h; Inert atmosphere; Reflux;

DOI:10.1246/bcsj.20100076

upstream raw materials:

Trimethyl borate

(3-bromophenyl)(phenyl)sulfane

1-bromo-3-(2'-pyridylthio)benzene

water

Downstream raw materials:

1-(2'-pyridyl)-3-(2'-pyridylthio)benzene