ChemicalBook CAS DataBase List METHYL 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE

METHYL 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE synthesis

14synthesis methods

Product Name:METHYL 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE
CAS Number:653589-95-8
Molecular formula:C14H19BO4
Molecular Weight:262.11

610-94-6

73183-34-3

METHYL 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE

653589-95-8

Methyl o-bromobenzoate (2.15 g, 10 mmol), bis(pinacolato)diboron (3.05 g, 12 mmol), potassium acetate (3.92 g, 40 mmol), and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.49 g, 0.5 mmol) were sequentially added to 150 mL of dioxane under nitrogen atmosphere. The reaction mixture was heated to 85 °C and the reaction was stirred at this temperature for 12 hours. Upon completion of the reaction, the solvent dioxane was removed by distillation under reduced pressure. The residue was extracted with dichloromethane and the combined organic phases were washed three times with saturated aqueous sodium chloride solution. The organic phases were dried over anhydrous sodium sulfate and the dichloromethane was removed by distillation under reduced pressure to give the crude product. The crude product was purified by column chromatography, and the eluent was a mixed solvent of petroleum ether and dichloromethane (3:1, v/v) to give 2-methoxycarbonylphenylboronic acid pinacol ester as a white solid (1.25 g, 86% yield). The structure of the product was confirmed by 1H NMR, 13C NMR, mass spectrometry (MS) and elemental analysis.

610-94-6 Synthesis

610-94-6
312 suppliers
$13.00/25g

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

653589-95-8
133 suppliers
$19.00/1g

Yield: 86%

Reaction Conditions:

with palladium bis[bis(diphenylphosphino)ferrocene] dichloride;potassium acetate in 1,4-dioxane for 12 h;Inert atmosphere;

Steps:

2.1 (1) Preparation of Compound 5
Under nitrogen protection,Methyl o-bromobenzoate (2.15 g, 10 mmol),bis(pinacolato)diboron(3.05g, 12mmol),Potassium acetate (3.92 g, 40 mmol),[1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.49 g, 0.5 mmol)It was added to 150 mL of dioxane and heated to 85 ° C for 12 hours.After the completion of the reaction, the dioxane was removed by distillation under reduced pressure, and the product was extracted with dichloromethane.Washed three times with saturated aqueous sodium chloride solution,After distilling off the dichloromethane under reduced pressure,The crude product was purified by column chromatography eluting with petroleum ether: methylene chloride = 3:1 (v/v) to give a solid, 2.25 g, yield 86%.The results of 1H NMR, 13C NMR, MS and elemental analysis indicated that the obtained compound was the object product.

References:

South China Xietong Chuangxin Institute;Ying Lei;Peng Feng;Zhong Zhiming;Huang Fei;Cao Yong CN108424344, 2018, A Location in patent:Paragraph 0062; 0063; 0064; 0074

610-97-9 Synthesis