ChemicalBook CAS DataBase List 4-(Bromomethyl)benzeneboronic acid pinacol ester

4-(Bromomethyl)benzeneboronic acid pinacol ester synthesis

13synthesis methods

Product Name:4-(Bromomethyl)benzeneboronic acid pinacol ester
CAS Number:138500-85-3
Molecular formula:C13H18BBrO2
Molecular Weight:297

Pinacol p-tolueneborate (10.91g, 50.0mmol), bromosuccinimide (NBS, 9.91g, 55.0mmol), and azobisisobutyronitrile (AIBN, 0.44g, 2.0mmol) were dissolved in dry of carbon tetrachloride (CCl4, 200 mL), stirred at reflux for 14 hours. The mixture was filtered, the solvent was evaporated, and the mixture was dissolved in ethyl acetate (200 mL). Wash once with distilled water (100 mL) and saturated sodium chloride aqueous solution (100 mL), dry with anhydrous sodium sulfate, and rotary evaporate. Finally, use petroleum ether as the eluent for column chromatography separation to obtain 4-(Bromomethyl)benzeneboronic acid pinacol ester (11.30g, yield 76.1%).

128-08-5 Synthesis

128-08-5
847 suppliers
$5.00/5 g

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

195062-57-8
155 suppliers
$5.00/250mg

4-(Bromomethyl)benzeneboronic acid pinacol ester

138500-85-3
261 suppliers
$8.00/1g

Yield:138500-85-3 76.1%

Reaction Conditions:

with 2,2'-azobis(isobutyronitrile) in tetrachloromethane for 14 h;Reflux;

Steps:

4
P-toluene boronic acid pinacol ester (10.91 g, 50.0 mmol),Bromosuccinimide (NBS, 9.91 g, 55.0 mmol),Azobisisobutyronitrile (AIBN, 0.44 g, 2.0 mmol) was dissolved in dry carbon tetrachloride (CCl4, 200 mL).It was stirred at reflux for 14 hours, filtered, the solvent was removed by rotary evaporation, and the ethyl acetate (200 mL) was dissolved.After washing once with distilled water (100 mL) and saturated aqueous sodium chloride solution (100 mL), it was dried over anhydrous sodium sulfate.Spin-steaming, finally using petroleum ether as eluent to cross the column,4-Bromomethylphenylboronic acid pinacol ester (11.30 g, yield 76.1%) was isolated.

References:

Nankai University;Li Changhua;Chen Haoliang CN107417714, 2017, A Location in patent:Paragraph 0056; 0057; 0061

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302348-51-2 Synthesis