5-(Aminomethyl)-2-chlorophenylboronic Acid Pinacol Ester synthesis
- Product Name:5-(Aminomethyl)-2-chlorophenylboronic Acid Pinacol Ester
- CAS Number:1544673-71-3
- Molecular formula:C13H19BClNO2
- Molecular Weight:267.56
![1H-Isoindole-1,3(2H)-dione, 2-[[4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]-](/CAS/20210305/GIF/1544673-54-2.gif)
1544673-54-2
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1544673-71-3
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Yield:1544673-71-3 36%
Reaction Conditions:
with hydrazine hydrate in tetrahydrofuran; for 12 h;Reflux;
Steps:
[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine (4a).
General procedure: Compound 3a (196 mg, 0.54 mmol) was added to a dry flask containing magnetic stir and dissolved in THF (5.50 mL). Afterwards, hydrazine hydrate (0.08 mL, 1.62 mmol) was added to the reaction mixture. The reaction was stirred under a reflux for 12 h. The resulting dried crude material was then re-suspended with chloroform (50.00 mL), filtered, and the filtrate was concentrated in vacuo. The crude material was purified by High Performance Liquid Chromatography (HPLC) to give the desired product 4a as a white solid (m.p. 85 °C) in 87% yield (111 mg); 1H-NMR (CDCl3) δ ppm 7.78 (d, J = 7.9 Hz, 2H),7.32 (d, J = 8.0 Hz, 2H), 3.88 (s, 2H), 1.34 (s, 12H); 13C-NMR (CDCl3) δ ppm 136.72, 135.56, 127.18,84.11, 43.94, 25.02; 11B-NMR (CD3OD-d4) δ ppm 30.90; HRMS (ESI, positive ion) (m/z): [M+H]+calcd for C13H20BNO2, 234.1669; found, 234.1651.
References:
Chung, Sheng-Hsuan;Lin, Ting-Ju;Hu, Qian-Yu;Tsai, Chia-Hua;Pan, Po-Shen [Molecules,2013,vol. 18,# 10,p. 12346 - 12367]
1150114-78-5
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1544673-71-3
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1544673-40-6
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