Preparation method of benzoheterocyclic-3-boric acid
A technology of benzoheterocycle and boronic acid, which is applied in the field of organic synthesis, can solve the complex synthesis of indole-3-boronic acid and other problems, and achieve the effect of simple synthesis route, high yield and easy purification of isomers
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Embodiment 1
[0023] In the reaction flask, add benzothiophene (13.4g, 0.1mol) and dichloromethane 140mL, stir well, then add BPh 3 (2.59g, 0.01mol), stirred at room temperature for 30 minutes. Cool to 0°C, start adding BBr dropwise 3 (26.3g, 0.105mol) / dichloromethane (70mL) solution. During the dropwise addition process, the reaction started to exotherm, and the reaction system was controlled not to exceed 20°C during the whole process, and the dropwise addition was completed in about 1.5 hours. After the dropwise addition was completed, the reaction was stirred overnight at room temperature. After sampling and quenching, TLC detected that the starting material disappeared.
[0024] Add the reaction solution dropwise into 1.0M aqueous sodium hydroxide solution. After the dropwise addition, continue to stir the reaction for 2-3 hours by introducing air, and detect the pH=12-13. Separate the organic layer and discard it. The water layer is adjusted with 10% hydrochloric acid. pH=2-3, extr...
Embodiment 2
[0026] In the reaction flask, add benzofuran (11.8g, 0.1mol) and dichloromethane 160mL, stir well, then add B(C 6 f 5 ) 3 (5.11g, 0.01mol), stirred at room temperature for 30 minutes. Cool to 0°C, start adding BBr dropwise 3 (26.3g, 0.105mol) / dichloromethane (70mL) solution. During the dropwise addition process, the reaction started to exotherm, and the reaction system was controlled not to exceed 20°C during the whole process, and the dropwise addition was completed in about 2.0 hours. After the dropwise addition was completed, the reaction was stirred overnight at room temperature. After sampling and quenching, TLC detected that the starting material disappeared.
[0027] Add the reaction solution dropwise into 1.0M potassium hydroxide aqueous solution. After the dropwise addition, continue to stir the reaction for 1 hour by introducing air, and detect the pH=12-13. Separate the organic layer and discard it. The aqueous layer is adjusted to pH= 2-3, extract twice with e...
Embodiment 3
[0029] In the reaction flask, add benzothiophene (13.4g, 0.1mol) and dichloromethane 220mL, stir well, then add BPh 3 (2.59g, 0.01mol), stirred at room temperature for 30 minutes. Cool to 0°C, start feeding BCl 3 (15.2 g, 0.13 mol) gas. During the feeding process, the reaction started to exotherm, and the reaction system was controlled not to exceed 20°C during the whole process, and the feeding was completed in about 2 hours. After the feeding is completed, the reaction bottle is sealed to maintain a certain pressure for reaction. Subsequently, the reaction was stirred overnight at room temperature, and after sampling and quenching, TLC detected that the starting material disappeared.
[0030] Add the reaction solution dropwise into 1.0M aqueous sodium hydroxide solution. After the dropwise addition, continue to stir the reaction for 2-3 hours by introducing air, and detect the pH=12-13. Separate the organic layer and discard it. The water layer is adjusted with 10% hydroc...
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