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ChemicalBook CAS DataBase List N-(2-BroMophenyl)-9H-carbazole
902518-11-0

N-(2-BroMophenyl)-9H-carbazole synthesis

6synthesis methods
Carbazole

86-74-8

1,2-Dibromobenzene

583-53-9

N-(2-BroMophenyl)-9H-carbazole

902518-11-0

(1) Carbazole (8.36 g, 0.05 mol), 1,2-dibromobenzene (17.69 g, 0.075 mol) and potassium carbonate (17.97 g, 0.13 mol) were added to a reactor under the protection of nitrogen and stirred thoroughly. Subsequently, cuprous iodide (1.91 g) and L-lysine (1.46 g) were added to the system, heated to 163 °C and maintained for 38 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) until the feedstock was completely consumed. Upon completion of the reaction, the reaction was quenched by the addition of large amounts of water and the solid product was precipitated by stirring. The solid was collected by filtration and dried to give 13.37 g of 9-(2'-bromophenyl)carbazole in 83% yield.

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Yield:902518-11-0 96%

Reaction Conditions:

with tripotassium phosphate tribasic;copper (I) iodide;(±)-trans-1,2-diaminocyclohexane in toluene; for 4 h;

Steps:

A1-1 Synthesis of Intermediate A(1)-P3

Carbazole (40 g, 1 eq.), 1-bromo-2-iodobenzene (70 g, 1.5 eq.), CuI (6.3 g, 0.2 eq.), K3PO4 (70 g, 2 eq.), trans-1,2-cyclohexanediamine (19 g, 1 eq.) and toluene (600 ml) were introduced to a 1-neck-round bottom flask (1-neck-r.b.f), and stirred for 4 hours. (0137) The reaction solution completed with the stirring was filtered only with methylene chloride (MC), and then column separated to obtain P3 (approximately 65 g). (0138) Step yield=96%

References:

US2022/106332,2022,A1 Location in patent:Paragraph 0135-0138

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