ChemicalBook CAS DataBase List (4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol synthesis

8synthesis methods

Product Name:(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol
CAS Number:302348-51-2
Molecular formula:C13H19BO3
Molecular Weight:234.1

873-75-6

73183-34-3

(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

302348-51-2

Using 4-bromobenzyl alcohol (compound 1, 1.0 g, 5.35 mmol) and pinacol ester of bisboronic acid (247 mg, 5.88 mmol) as raw materials, compound 1 was dissolved in 10 mL of anhydrous 1,4-dioxane under nitrogen protection, and potassium acetate and PdCl2 (Dppf) were added as catalysts. The reaction mixture was heated to 85 °C and stirred until the reaction was complete (monitored by thin layer chromatography). After completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was extracted by adding ethyl acetate (200 mL) to the residue. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (mobile phase: ethyl acetate/petroleum ether = 1:8 to 1:4) to afford 181 mg of a light yellow oily liquid, 4-(hydroxymethyl)benzeneboronic acid pinacol ester, in 90% yield.

128376-64-7 Synthesis

4-Formylphenylboronic acid pinacol cyclic ester

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

302348-51-2
131 suppliers
$5.00/250mg

Yield:302348-51-2 513 mg

Reaction Conditions:

with sodium tetrahydroborate at 20; for 5 h;

Steps:

[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol (2a).
To a mixture of a4-formylbenzenboronic acid (1a, 375 mg, 2.50 mmol), pinacol (355 mg, 3.00 mmol) and anhydrous magnesium sulfate (625 mg, 5.00 mmol), methanol was added (12.50 mL). The mixture was stirred at room temperature for 6 h. After the reaction was completed, the crude solution was filtered, and then sodium borohydride (47 mg, 1.25 mmol) was added to the filtrate. Afterwards, the reaction mixture was stirred for an additional 5 h. Once the reaction was completed, the reaction mixture was filtered and the filtrate was concentrated in vacuo to give the desired product 2a as a white solid (m.p. 75-77 °C) in88% yield (513 mg). ¹H-NMR (CD₃OD-d₄) δ ppm 7.71 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 7.8 Hz, 2H),4.62 (s, 2H), 1.34 (s, 12H); ¹³C-NMR (CD₃OD-d₄) δ ppm 146.23, 135.93, 127.26, 85.19, 65.24, 25.34;¹¹B-NMR (CDCl₃) δ ppm 34.82.

References:

Chung, Sheng-Hsuan;Lin, Ting-Ju;Hu, Qian-Yu;Tsai, Chia-Hua;Pan, Po-Shen [Molecules,2013,vol. 18,# 10,p. 12346 - 12367]

FullText

873-75-6 Synthesis

873-75-6
316 suppliers
$6.00/5g

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

302348-51-2
131 suppliers
$5.00/250mg

References