ChemicalBook CAS DataBase List B-[2-(9H-Carbazol-9-yl)phenyl]boronic acid

B-[2-(9H-Carbazol-9-yl)phenyl]boronic acid synthesis

8synthesis methods

Product Name:B-[2-(9H-Carbazol-9-yl)phenyl]boronic acid
CAS Number:1189047-28-6
Molecular formula:C18H14BNO2
Molecular Weight:287.12

In argon atmosphere, 9-(2-bromophenyl)-9H-carbazole in THF (124 mL) was cooled in a dry ice/acetone bath, to which a 1.6 M hexane solution of n-butyllithium (17.1 mL, 27.3 mmol) was added dropwise, and the resultant solution was stirred for 2 h. After adding a solution of trimethyl borate (3.33 mL, 29.8 mmol) in THF (10 mL) dropwise, the stirring was continued for one hour, and then, the dry ice/acetone bath was removed and the temperature was raised to room temperature. The reaction liquid was cooled in an iced water bath and stirred for one hour after adding a 2 M hydrochloric acid and then the temperature was raised to room temperature. The obtained reaction liquid was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was crystallized to obtain B-[2-(9H-Carbazol-9-yl)phenyl]boronic acid.

B-[2-(9H-Carbazol-9-yl)phenyl]boronic acid

5419-55-6
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$12.00/5g

902518-11-0 Synthesis

902518-11-0
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$9.00/250mg

1189047-28-6
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$100.00/1g

Yield:1189047-28-6 90%

Reaction Conditions:

Stage #1: 9-(2-bromophenyl)-9H-carbazolewith n-butyllithium in tetrahydrofuran at -78; for 1.5 h;Inert atmosphere;
Stage #2: Triisopropyl borate in tetrahydrofuran at 20; for 8 h;

Steps:

1.2 2 Synthesis of ((2-(9H-carbazol-9-yl)phenyl)boronicacid):

9-(2-Bromophenyl)-9H-carbazole (1 eq), added to a dry tetrahydrofuran solution, cooled to -78 ° C, and exchanged N2 three times to ensure the system's oxygen-free environment.After adding n-butyllithium (2.5 M, 1.1 eq) dropwise, the reaction was kept at -78 ° C for 1.5 h.Triisopropyl borate (ρ=0.815g/ml, 1.1eq) was added dropwise, and the mixture was added to room temperature after the addition was completed. After 8 hours, the reaction was quenched with dilute hydrochloric acid.The tetrahydrofuran was distilled off under reduced pressure, dissolved in dichloromethane, washed with water, anhydrous magnesium sulfate, dried, filtered, and the filtrate was recrystallized.Obtained a white solid product (90%);

References:

CN108285452,2018,A Location in patent:Paragraph 0035; 0064; 0076; 0077