ChemicalBook CAS DataBase List 4-Carboxylphenylboronic acid pinacol ester

4-Carboxylphenylboronic acid pinacol ester synthesis

12synthesis methods

Product Name:4-Carboxylphenylboronic acid pinacol ester
CAS Number:180516-87-4
Molecular formula:C13H17BO4
Molecular Weight:248.08

150-13-0

73183-34-3

4-Carboxylphenylboronic acid pinacol ester

180516-87-4

GENERAL METHODS: Tert-butyl nitrite (155 mg, 1.1 mmol) was added dropwise to a mixture containing bis(pinacolato)diboron (127 mg, 0.5 mmol), p-aminobenzoic acid (61 mg, 0.5 mmol) and eosin Y (0.01 mmol). The reaction mixture was stirred in acetonitrile (3 mL) under blue LED irradiation for 2 h at room temperature (the progress of the reaction was monitored by TLC). Upon completion of the reaction, the mixture was diluted with ethyl acetate (5 mL) and then filtered through diatomaceous earth. The filtrate was extracted with ethyl acetate (3 x 10 mL) and the combined organic phases were washed with saturated saline and dried over anhydrous Na2SO4. Concentration under reduced pressure afforded the crude product, which was purified by silica gel column chromatography using hexane-ethyl acetate (98:2) as eluent to afford pure 4-carboxyphenylboronic acid pinacol ester as a pale yellow viscous liquid (208 mg, 88% yield).IR (pure samples)2978, 2933, 2839, 2526, 2050, 1950, 1911, 1724, 1605, 1570 cm-1; 1H NMR (500 MHz, CDCl3) δ 1.33 (s, 12H), 7.82 (s, 3H), 6.89 (d, J = 8.0 Hz, 2H), 7.75 (d, J = 8.0 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 24.9 (4C), 55.2, 83.6 (2C), 113.4 (2C), 136.6 (2C), 162.3.The spectral data of the obtained compounds are in agreement with the 4-carboxyphenylboronic acid pinacol ester reported in the literature.

76-09-5 Synthesis

76-09-5
400 suppliers
$8.19/250mg

14047-29-1
476 suppliers
$10.00/5 g

180516-87-4
247 suppliers
$8.00/1g

Yield:180516-87-4 93.7%

Reaction Conditions:

in hexane at 70; for 3 h;Temperature;Time;Concentration;

Steps:

1
To a 500 mL reaction flask was added p-carboxyphenylboronic acid (50 g, 0.3 mol), pinacol (39 g, 0.33 mol), n-hexane 100 g, and the temperature was raised to 70 ° C, and the reaction was carried out for 3 hours, and concentrated under reduced pressure. Drying in vacuo gave 73 g of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid as a white solid. Yield: 98%.

References:

Zhejiang Keju Bio-pharmaceutical Co., Ltd.;Yang Yong;Yang Ming;Shen Chao;Wang Dong CN109053780, 2018, A Location in patent:Paragraph 0021; 0038; 0041; 0047; 0053; 0059; 0065; 0071

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150-13-0 Synthesis

150-13-0
953 suppliers
$5.00/25g

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

180516-87-4
247 suppliers
$8.00/1g

References