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ChemicalBook CAS DataBase List 4-(9H-Carbozol-9-yl)phenylboronic acid

4-(9H-Carbozol-9-yl)phenylboronic acid synthesis

14synthesis methods
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Yield:419536-33-7 86%

Reaction Conditions:

Stage #1:N-(4-bromophenyl)carbazole with n-butyllithium in tetrahydrofuran;hexane for 1 h;Inert atmosphere;
Stage #2:Triisopropyl borate in tetrahydrofuran;hexaneInert atmosphere;

Steps:

2.4.2. Synthesize of (4-(9H-carbazol-9-yl) phenyl) boronic acid (Cz-PhB(OH)2)
Cz-PhBr (15 mmol) was solved into THF in flask with gasreplacement by Ar for three times. After cooling down to 78 °C for10 min. N-butyl lithium (t-BuLi, 11 mL, 1.6 mol L1 in hexane solution)was dropped into and stirred for 1 h at 78 °C. The Triisopropylborate (23 mmol) was dropped into flask and stirred foranother 1 h at 78 °C the slowly warmed to room temperature andstirred overnight. Hydrochloric acid (HCl, 30 mL, 2 mol L1) wasadded into the flask and stirred for another 30 min. The productswas extracted by Dichloromethane (CH2Cl2). After evaporation, thecrude product was washed with pure petroleum ether. A whitepowder achieved with yield of 86%.

References:

Wang, Panpan;Fan, Shigen;Liang, Junfei;Ying, Lei;You, Jing;Wang, Shirong;Li, Xianggao [Dyes and Pigments,2017,vol. 142,p. 175 - 182]

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