ChemicalBook CAS DataBase List 4-Formylphenylboronic acid pinacol cyclic ester

4-Formylphenylboronic acid pinacol cyclic ester synthesis

12synthesis methods

Product Name:4-Formylphenylboronic acid pinacol cyclic ester
CAS Number:128376-64-7
Molecular formula:C13H17BO3
Molecular Weight:232.08

1122-91-4

73183-34-3

4-Formylphenylboronic acid pinacol cyclic ester

128376-64-7

General procedure for the synthesis of 4-formylphenylboronic acid pinacol ester from p-bromobenzaldehyde and pinacol ester of biboronic acid: to a stirred solution of p-bromobenzaldehyde (8 g, 0.15 mol), pinacol ester of biboronic acid (45.7 g, 0.18 mol), and Pd(dppf)Cl2 (5.26 g, 7.5 mmol) in 1,4-dioxane, under argon protection, was KOAc (22.0 g, 0.225 mol) was added. The reaction mixture was stirred at 80 °C for 15 min. After completion of the reaction, the solvent was removed under reduced pressure. The residue was diluted with petroleum ether (500 mL) and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by fast chromatography (silica gel, petroleum ether/ethyl acetate, 10:1) to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxolan-2-yl)benzaldehyde (32.5 g, 95% yield) as a white solid.

1122-91-4
694 suppliers
$9.00/10g

73183-34-3
585 suppliers
$6.00/5g

128376-64-7
190 suppliers
$5.00/250mg

Yield:128376-64-7 96%

Reaction Conditions:

with palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride;anhydrous potassium acetate in 1,4-dioxane;Reflux;Inert atmosphere;Suzuki Coupling;

Steps:

General procedure B

General procedure: (for the synthesis of compounds 5, 31, 42 and 45) [1,1' -bis (diphenylphosphine) ferrocene] palladium dichloride (200mg, 0.27mmol), and potassium acetate (1.589g, 16.2mmol) was added into 30mL 1,4-dioxane solution of bromobenzene (5.4mmol) and Bis(pinacolato)diboron (1.647g, 6.49mmol). The mixture was heated to reflux overnight under a nitrogen atmosphere. After extraction and concentrated, the residue was purified by column chromatography to afford the product.

References:

Wu, Yizhe;Zhang, Yu;Guo, Yu;Pan, Zhichao;Zhong, Shichun;Jin, Xinxin;Zhuang, Weihao;Chen, Sikang;Gao, Jian;Huang, Wenhai;Dong, Xiaowu;Che, Jinxin [European Journal of Medicinal Chemistry,2021,vol. 223,art. no. 113637]

302348-51-2 Synthesis