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Synthetic method for 9,10-benzophenanthrene compound

A synthesis method and compound technology, applied in the preparation of organic compounds, chemical instruments and methods, and hydrocarbon production from halogen-containing organic compounds, etc., can solve the problems of many steps and harsh conditions, and achieve short reaction time, high yield, The effect of good application prospects

Active Publication Date: 2017-10-20
LILY GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Therefore, in view of the problem that there are many steps and harsh conditions in the method for synthesizing triphenylene in the prior art, the object of the present invention is to provide a kind of 9,10-triphenylene with diaryliodonium salt as arylation reagent. The synthetic method of compound

Method used

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  • Synthetic method for 9,10-benzophenanthrene compound
  • Synthetic method for 9,10-benzophenanthrene compound
  • Synthetic method for 9,10-benzophenanthrene compound

Examples

Experimental program
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Effect test

Embodiment 1

[0032]

[0033] Phenylboronic acid (1a, 12mmol, 1.2equiv) and potassium carbonate (15mmol, 1.5equiv) and bistriphenylphosphine palladium dichloride (0.2mmol, 0.02equiv) were placed in a 100mL round bottom flask, and 30mL of DME ( Ethylene glycol dimethyl ether) and 6mL H 2O, add o-bromoiodobenzene (10mmol, 1.0equiv) and heat to 80°C for 6 hours. After the reaction, cool to room temperature, add 50 mL of water to quench the reaction, extract three times with 100 mL of ethyl acetate, dry the organic phase with anhydrous sodium sulfate, filter and spin to dry column chromatography (eluent: PE) to obtain compound 2a.

[0034] N 2 Under protection, in a 25mL Schlenk bottle, add diaryliodonium salt (0.3mmol, 1.5equiv), Cu(OTf) 2 (0.01mmol, 3.61mg), Na 2 CO 3 (0.4mmol, 2.0equiv) and CsOAc (0.6mmol, 3.0equiv), the reaction substrate 2a (0.2mmol, 1.0equiv) and 4mL redistilled DMF were added by syringe, and reacted at 130°C for 12 hours. After the reaction, the solvent was spin-...

Embodiment 2

[0037]

[0038] 4-Methylphenylboronic acid (1b, 12mmol, 1.2equiv) and potassium carbonate (15mmol, 1.5equiv) and ditriphenylphosphine palladium dichloride (0.2mmol, 0.02equiv) were placed in a 100mL round bottom flask, while Add 30mL DME (ethylene glycol dimethyl ether) and 6mL H 2 O, add o-bromoiodobenzene (10mmol, 1.0equiv) and heat to 80°C for 6 hours. After the reaction, cool to room temperature, add 50 mL of water to quench the reaction, extract three times with 100 mL of ethyl acetate, dry the organic phase with anhydrous sodium sulfate, filter and spin dry column chromatography (eluent: PE) to obtain compound 2b.

[0039] N 2 Under protection, in a 25mL Schlenk bottle, add diaryliodonium salt (0.3mmol, 1.5equiv), Cu(OTf) 2 (0.01mmol, 3.61mg), Na 2 CO 3 (0.4mmol, 2.0equiv) and CsOAc (0.6mmol, 3.0equiv) were added to reaction substrate 2b (0.2mmol, 1.0equiv) and 4mL redistilled DMF by syringe, and reacted at 130°C for 12 hours. After the reaction, the solvent was ...

Embodiment 3

[0042]

[0043] 2-Methylphenylboronic acid (1c, 12mmol, 1.2eeqquiv) and potassium carbonate (15mmol, 1.5equiv) and ditriphenylphosphine palladium dichloride (0.2mmol, 0.02equiv) were placed in a 100mL round-bottomed flask while Add 30mL DME (ethylene glycol dimethyl ether) and 6mL H 2 O, add o-bromoiodobenzene (10mmol, 1.0equiv) and heat to 80°C for 6 hours. After the reaction, cool to room temperature, add 50 mL of water to quench the reaction, extract three times with 100 mL of ethyl acetate, dry the organic phase with anhydrous sodium sulfate, filter and spin to dry column chromatography (eluent: PE) to obtain compound 2c.

[0044] N 2 Under protection, in a 25mL Schlenk bottle, add diaryliodonium salt (0.3mmol, 1.5equiv), Cu(OTf) 2 (0.01mmol, 3.61mg), Na 2 CO 3 (0.4mmol, 2.0equiv) and CsOAc (0.6mmol, 3.0equiv) were added to reaction substrate 2c (0.2mmol, 1.0equiv) and 4mL redistilled DMF with a syringe, and reacted at 130°C for 12 hours. After the reaction was com...

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Abstract

The invention discloses a synthetic method for a 9,10-benzophenanthrene compound. The synthetic method comprises the following concrete steps: dissolving a compound as shown in a formula (2) which is described in the specification and another compound as shown in a formula (4) which is described in the specification in N,N-dimethyl formamide under the protection of inert gas; and carrying out a reaction at 120 to 140 DEG C under the action of copper trifluoromethanesulfonate, sodium carbonate and caesium acetate so as to obtain the 9,10-benzophenanthrene compound as shown in a formula (I) which is described in the specification. According to the invention, 2-bromobiphenyl is used as a raw material, diaryl iodate is used as an arylation reagent, bivalent copper is used as a catalyst, and sodium carbonate and caesium acetate are used as mixed base; the synthetic method has the characteristics of usage of easily available raw materials, short reaction time, high yield, etc.; and as a simplest graphene monomer, the synthesized 9,10-benzophenanthrene compound good application prospects in the field of organic photoelectricity.

Description

technical field [0001] The invention relates to the technical field of synthesis of organic compounds, in particular to a synthesis method of 9,10-triphenylene compounds. Background technique [0002] In the 21st century, with the rapid development of functional materials and biomedicine, organic functional materials with large π-conjugated systems have many applications in optoelectronics and other fields. Polycyclic aromatic hydrocarbons (PAH), as a typical large π-conjugated system compound, can control the key performance of some functional materials in the field of optoelectronics. Among the fused-ring aromatic hydrocarbons, 9,10-triphenylene is the smallest graphene monomer, and its synthesis method has also attracted the attention of many scientists all over the world. At present, there are many methods for synthesizing triphenylene, but there are many synthetic steps and harsh conditions. Contents of the invention [0003] Therefore, in view of the problem that t...

Claims

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Application Information

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IPC IPC(8): C07D311/94C07C1/28C07C15/38C07C17/269C07C25/22C07C22/08C07C41/30C07C43/20C07C201/12C07C205/06C07C253/30C07C255/52
CPCC07C1/28C07C17/263C07C17/269C07C41/30C07C201/12C07C253/30C07D311/94C07C15/38C07C25/22C07C22/08C07C43/20C07C205/06C07C255/52C07C25/18C07C43/225C07C205/12C07C255/50
Inventor 王利民吴洵燊汪钰唐智聪舒雅键徐萌王峰王桂峰韩建伟田禾陈立荣黄卓
Owner LILY GRP CO LTD
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