
(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol synthesis
- Product Name:(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol
- CAS Number:443776-76-9
- Molecular formula:C13H19BO3
- Molecular Weight:234.1

380151-86-0

443776-76-9
GENERAL METHOD: Methanol (12.50 mL) was added to a mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (1a, 375 mg, 2.50 mmol), pinacol (355 mg, 3.00 mmol) and anhydrous magnesium sulfate (625 mg, 5.00 mmol). The mixture was stirred at room temperature for 6 hours. Upon completion of the reaction, the crude reaction mixture was filtered and then sodium borohydride (47 mg, 1.25 mmol) was added to the filtrate. Subsequently, the reaction mixture was stirred for another 5 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated in vacuum to afford the target product 3-hydroxymethylphenylboronic acid pinacol ester (2a) as a white solid (melting point 75-77 °C) in 88% 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) δppm: 146.23, 135.93, 127.26, 85.19, 65.24, 25.34; 11B-NMR (CDCl3) δppm: 34.82.

380151-86-0
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$14.00/1g

443776-76-9
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$8.00/250mg
Yield:443776-76-9 502 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).
General procedure: 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]

480425-35-2
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443776-76-9
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$8.00/250mg

76-09-5
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$8.19/250mg

87199-15-3
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443776-76-9
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87199-16-4
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443776-76-9
107 suppliers
$8.00/250mg

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

443776-76-9
107 suppliers
$8.00/250mg