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(E)-3-(4-bromostyryl)-9-phenyl-9H-carbazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.25h;Inert atmosphere;
<strong>[87220-68-6]9-phenyl-9H-carbazole-3-carbaldehyde</strong> (3 52 g, 13 mmol) was reacted with (diethyl 4-bromobenzyl) phosphonate (4 42 g, 14.4 mmol) was placed In a two-necked flask, evacuate and pass nitrogen and add 20 m of anhydrous tetrahydrofuran (THF). Under ice bath, potassium tert-butoxide (t-BuOK X 3.36 g, 30 mmol) dissolved in THF (30 mL) Add slowly to the mixture at 0 C for 15 minutes. The solvent was removed by concentration under reduced pressure and the column was reused (N-hexane: dichloromethane = 5: 1) to give the white intermediate 1-4 ((E) -3- (4-bromostyryl) -9-phenyl-9H-carbazole) (4.52 g, yield 82%).
63%
With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.25h;Inert atmosphere;
<strong>[87220-68-6]9-phenyl-9H-carbazole-3-carbaldehyde</strong> (3.52 g, 13 mmol) and diethyl 4-bromobenzyl phosphonate (4.42 g, 14.4 mmol) was added to a solution placed in a two-necked flask, evacuated and passed through nitrogen, 20 m L of anhydrous tetrahydrofuran (THF) was added; Potassium tert-butoxide (t-BuOK) (3.36 g, 30 mmol) dissolved in THF (30 mL) was added slowly under ice-cooling, Reaction at 0 C for 15 minutes. The solvent was removed by concentration under reduced pressure and purified by column chromatography (n-hexane: dichloromethane = 5: 1) to give a white intermediate I-4 ((E) -3- (4-bromostyryl) -9-phenyl-9H-carbazole) (4.52 g, yield 82%).
With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 24h;Inert atmosphere;
Potassium t-butoxide (t-BuOK) (0.22 g, 2 mmol) was placed in a two-necked flask, evacuated and nitrogen was introduced, and 3 mL of anhydrous tetrahydrofuran (THF) was added. A mixture of 4- (9H-carbazol-9-yl) benzaldehyde (0.27 g, 1 mmol) and diethyl 4-bromobenzylphosphate (diethyl Bromobenzyl phosphonate (0.34 g, 1.1 mmol) was placed in a single neck flask and 3 mL of anhydrous tetrahydrofuran was added under a nitrogen atmosphere. The solution in the flask was slowly added to the two-necked flask under ice-cooling and mixed and reacted at 0 C for 1 day. The reaction solution was poured into water to precipitate a yellow solid. The precipitated yellow solid was filtered and the intermediate product I-5 ((E) -9- (4- (4-bromostyryl) phenyl) -9H-carbazole was obtained by repeatedly washing with methanol to obtain a pale yellow powder. (0.39 g, yield 93%).
93%
With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.25h;Inert atmosphere;
Potassium t-butoxide (t-BuOK) (0.22 g, 2 mmol) was placed in a two-necked flask, evacuated and nitrogen was introduced, and 3 mL of anhydrous tetrahydrofuran (THF) was added. A mixture of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (0.27 g, 1 mmol) and diethyl 4-bromobenzyl phosphonate (0.34 g, 1.1 mmol) placed in a single neck flask, in the nitrogen environment by adding 3mL of anhydrous tetrahydrofuran. The solution in the flask was slowly added to the flask and mixed under ice bath and reacted at 0 C for 1 day. The reaction solution was poured into water to precipitate a yellow solid. The precipitated yellow solid was evacuated and filtered, and repeatedly washed with methanol to obtain the intermediate product of the pale yellow powder I-5 ((E)-9-(4-(4-bromostyryl)phenyl)-9H-carbazole (0.39 g, yield 93%).
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