4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENYLBORONIC ACID synthesis
- Product Name:4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENYLBORONIC ACID
- CAS Number:159191-56-7
- Molecular formula:C12H21BO3Si
- Molecular Weight:252.19
71597-85-8
333 suppliers
$6.00/1g
18162-48-6
692 suppliers
$9.00/5g
159191-56-7
123 suppliers
$20.00/250mg
Yield: 90%
Reaction Conditions:
with 1H-imidazole in N,N-dimethyl-formamide at 20; for 12 h;
Steps:
(4-((tert-Butyldimethylsilyl)oxy)phenyl)boronic Acid (9)
To a solution of 4-hydroxyphenylboronic acid (1.0 equiv., 5 mmol) in dry DMF (0.05 M) was added imidazole (5.0 equiv.) at rt, followed by the addition of TBSCl (3.5 equiv.). The reaction mixture was stirred at rt for 12 h; after completion monitored by TLC, the mixture was extracted with ethyl acetate (330 mL) and water (50 mL), and the organic layers were dried over MgSO4 and concentrated under vacuum. The residue was purified by flash chromatography (hexane/ethyl acetate 10 : 1 → 3 : 1) to give the product as a white solid (2.27 g, 90% yield). Rf (hexane/ethyl acetate 1 : 1) 0.30. δH (300 MHz, CDCl3) 8.11 (2H, d, J 8.4), 6.96 (2H, d, J 8.4), 1.02 (9H, s), 0.26 (6H, s). δC (75 MHz, CDCl3) 159.9, 137.6, 119.9, 111.0, 25.8, 18.4, 4.2. The spectroscopic data matched those reported in the literature.[15]
References:
Zhou, Qingqing;Reekie, Tristan A.;Abbassi, Ramzi H.;Venkata, Dinesh Indurthi;Font, Josep S.;Ryan, Renae M.;Rendina, Louis M.;Munoz, Lenka;Kassiou, Michael [Australian Journal of Chemistry,2018,vol. 71,# 10,p. 789 - 797]
67963-68-2
135 suppliers
$17.00/1g
159191-56-7
123 suppliers
$20.00/250mg
5419-55-6
388 suppliers
$12.00/5g
67963-68-2
135 suppliers
$17.00/1g
159191-56-7
123 suppliers
$20.00/250mg
18162-48-6
692 suppliers
$9.00/5g
159191-56-7
123 suppliers
$20.00/250mg
121-43-7
376 suppliers
$13.00/25mL
67963-68-2
135 suppliers
$17.00/1g
159191-56-7
123 suppliers
$20.00/250mg