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Method for synthesizing carbazole derivative

A technology of carbazole derivatives and synthesis methods, which is applied in chemical instruments and methods, chemical/physical processes, physical/chemical process catalysts, etc., can solve the problems of limited functional group compatibility, rare raw material substrates, unfriendly environment, etc. To achieve the effect of simple operation, mild reaction conditions and a wide range of substrates

Inactive Publication Date: 2011-06-08
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Such as: route (5) reaction step is more, route (1) and (3) (4) raw material substrate is rare, route (1) (5) reaction needs strong acid, thus has limited the compatibility of functional group, route (3) Use chromium reagent, not friendly to the environment

Method used

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  • Method for synthesizing carbazole derivative
  • Method for synthesizing carbazole derivative
  • Method for synthesizing carbazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of 9-Acetylcarbazole

[0029] Add iodobenzene (0.2mmol, 40.8mg), acetanilide (0.2mmol, 27mg), PdCl to the dry reaction tube 2 (0.01mmol, 2.2mg), CuF 2 (0.1mmol, 10.1mg), AgBr (0.2mmol, 37.2g), add solvent 2mL 1,4-dioxane, heat to reflux for 48h., filter after the reaction, the filtrate is distilled to remove the solvent, and the residue is purified by silica gel column layer Analysis, rinse with a mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:20, collect the effluent according to time gradient, TLC detection, combine the effluent containing carbazole derivatives, distill off the solvent with a rotary evaporator, and dry in vacuo Finally, 37.6 mg of white flaky solid was obtained with a yield of 90.1%. 1 H NMR (300MHz, CDCl 3 ( dt, J=7.5, 1.0Hz, 2H), 2.88(s, 3H); 13 C NMR (CDCl 3 )δ170.0, 138.5, 127.3, 126.3, 123.6, 119.7, 116.2, 27.6.

Embodiment 2

[0031] Synthesis of 9-Acetyl-2-methylcarbazole

[0032] Add 0.24mmol of 3-methyliodobenzene to the dry reaction tube, 0.2mmol of acetanilide, Pd(OAc) 2 0.01mmol, CuF 2 0.1mmol, AgBr 0.2mmol, add 3mL of solvent 1,4-dioxane, heat and reflux for 48h. After the reaction is completed, filter, the filtrate is distilled to remove the solvent, and the residue is subjected to silica gel column chromatography. The volume ratio of ethyl acetate and petroleum ether is The mixed solution of 1:20 was rinsed, the effluent was collected according to the time gradient, detected by TLC, the effluent containing the carbazole derivative was combined, the solvent was distilled off by a rotary evaporator, and 44 mg of a white flaky solid was obtained after vacuum drying, with a yield of 98%. %.

[0033] 1 H NMR (300MHz, CDCl 3)δ8.18(d, J=8.35Hz, 1H), 8.08(s, 1H), 7.97(d, J=7.65Hz, 1H), 7.88(d, J=7.82Hz, 1H), 7.46(td, J=7.82, 1.37Hz, 1H), 7.38(td, J=7.48, 0.96Hz, 1H), 7.23(d, J=7.86Hz, 1H), 2....

Embodiment 3

[0035] Synthesis of 9-Acetyl-2-tert-Butylcarbazole

[0036] Add 0.24 mmol of 3-tert-butyl iodobenzene, 0.2 mmol of acetanilide, and PdCl to the dry reaction tube 2 0.01mmol, CuF 2 0.1mmol, AgF 0.2mmol, add solvent 5mL toluene, heat and reflux for 48h. After the reaction is completed, filter, the filtrate is distilled to remove the solvent, and the residue is subjected to silica gel column chromatography, using a mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:20 Rinse, collect the effluent according to time gradient, TLC detection, combine the effluent containing the carbazole derivative, distill off the solvent with a rotary evaporator, and obtain 51 mg of a white flaky solid after vacuum drying, with a yield of 96%.

[0037] 1 H NMR (300MHz, CDCl 3 )δ8.35(s, 1H), 8.16(d, J=8.27Hz, 1H), 7.97(d, J=7.67Hz, 1H), 7.92(d, J=8.17Hz, 1H), 7.50-7.42( m, 2H), 7.38(t, J=7.47Hz, 1H), 2.90(s, 3H), 1.46(s, 9H). 13 C NMR (CDCl 3 )δ170.37, 151.30, 139.24...

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Abstract

The invention discloses a method for compounding a carbazole derivative. The method comprises the following steps: heating an iodobenzene derivative shown as the formula (I) and a phenylamide derivative shown as the formula (II) in organic solvent to reflux temperature to react by metal salt catalyst and completely reacting; after the reaction is finished, separating reaction liquid to obtain thecarbazole derivative shown as the formula (III), wherein the matter content ratio between the phenylamide derivative and the iodobenzene derivative is 1:1-3; the metal salt catalyst is a mixture mixed by palladium salt, copper salt and silver salt according to the matter content ratio of 0.05:0.5-1:0.5-2; and the ratio of the total matter content of metallic cations in the metal salt catalyst andthe matter content of the phenylamide derivative shown as the formula (II) is 1.05-3.05:1. The invention has the advantages of cheap and easily acquired raw material for use, simple and convenient operation, mild reaction condition, no strong acid condition needed and wide substrate range and can compound various acquired carbazole derivatives.

Description

technical field [0001] The invention relates to a method for synthesizing carbazole derivatives, in particular to a method for catalytically synthesizing carbazole derivatives with a transition metal salt catalyst. Background technique [0002] Carbazole is one of the important components of coal tar and an intermediate of many fine chemicals. It can be used to make leather plastics, pesticides, insecticides, medicines, rubber, etc. It is especially worth noting that carbazole has an important application in the dye industry. It can be used to synthesize carbazole blue dyes, azo dyes, anthraquinone dyes, methine dyes, etc., and these dyes can be used as photosensitive materials for photoelectric photography. Material. At the same time, carbazole is also used in synthetic pigments and pigments, and is widely used in the coloring of plastics, coatings, inks and fibers. With the development of the dye industry, the demand for carbazole is increasing year by year. [0003] Ca...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07D209/88B01J27/13B01J27/128B01J27/08
Inventor 杨东朋成江贾肖飞
Owner WENZHOU UNIV
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