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ChemicalBook CAS DataBase List [4-Fluoro-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine
1544673-68-8

[4-Fluoro-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine synthesis

5synthesis methods
1H-Isoindole-1,3(2H)-dione, 2-[[4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]-

1544673-52-0
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[4-Fluoro-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine

1544673-68-8
9 suppliers
$790.00/5g

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Yield:1544673-68-8 98%

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]

1333264-06-4 Synthesis
(4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

1333264-06-4
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[4-Fluoro-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine

1544673-68-8
9 suppliers
$790.00/5g

1112208-82-8 Synthesis
2-Fluoro-5-formylphenylboronic acid pinacol ester

1112208-82-8
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$37.70/250mg

[4-Fluoro-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine

1544673-68-8
9 suppliers
$790.00/5g