ChemicalBook CAS DataBase List 4-(TRIMETHYLSILYL)PHENYLBORONIC ACID

4-(TRIMETHYLSILYL)PHENYLBORONIC ACID synthesis

4synthesis methods

Product Name:4-(TRIMETHYLSILYL)PHENYLBORONIC ACID
CAS Number:17865-11-1
Molecular formula:C9H15BO2Si
Molecular Weight:194.11

6999-03-7 Synthesis

6999-03-7
119 suppliers
$14.00/1g

17865-11-1
170 suppliers
$8.00/250mg

Yield:17865-11-1 85%

Reaction Conditions:

Stage #1:1-bromo-4-(trimethylsilyl)benzene with n-butyllithium in tetrahydrofuran;hexane at -78; for 1.5 h;Inert atmosphere;
Stage #2: with Trimethyl borate in tetrahydrofuran;hexane at -78 - 20;
Stage #3: with water in tetrahydrofuran;hexane;ethyl acetate

Steps:

1
l-Bromo-4-(trimethylsilyl)benzene (25 g, 0.10 mol) was added to a 1-bulb flask and an argon atmosphere was established. After adding tetrahydrofuran (500 mL), the mixture was stirred at -78 ⁰C for 10 minutes. After adding n-BuLi (2.5 M in hexane, 43.6 mL, 0.10 mol) dropwise, the mixture was stirred for 1 hour and 30 minutes at -78 0C. Then, trimethyl borate (13.6 mL, 0.11 mol) was added at -78 ⁰C. After stirring for 30 minutes at -78 ⁰C, the mixture was stirred at room temperature for 4 hours. After the reaction was completed, extraction was performed using distilled water and EA. The organic layer was dried with MgSO₄ and the solvent was removed using a rotary evaporator. Pure Compound A (18 g, 85%) was separated by column chromatography using hexane and EA as an eluent.

References:

DOW ADVANCED DISPLAY MATERIALS, LTD.;YOON, Seung Soo;KIM, Sung Min;KIM, Bong Ok;KWON, Hyuck Joo;EUM, Sung Jin;CHO, Young Jun;LEE, Hyo Jung WO2010/140801, 2010, A1 Location in patent:Page/Page column 18

FullText