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A method for synthesizing fluorenone compounds by molecular oxygen oxidation in aqueous phase

A fluorene compound and a technology for synthesizing fluorenone, which are applied in the field of fluorenone compound synthesis, can solve problems such as organic solvent pollution, generation of by-products and the like, and achieve the effects of mild oxidation characteristics, easy separation, simple and safe post-processing

Active Publication Date: 2022-03-11
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The present invention aims at the technical problems of organic solvent pollution and generation of by-products in the method for synthesizing fluorenone compounds in the prior art, and provides a method for synthesizing fluorenone compounds by oxidation of molecular oxygen in the water phase. The present invention utilizes molecular oxygen as Oxidant, using water as a solvent, avoiding the use of organic solvents, and there is no problem of generating various by-products due to peroxidation

Method used

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  • A method for synthesizing fluorenone compounds by molecular oxygen oxidation in aqueous phase
  • A method for synthesizing fluorenone compounds by molecular oxygen oxidation in aqueous phase
  • A method for synthesizing fluorenone compounds by molecular oxygen oxidation in aqueous phase

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Experimental program
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Effect test

Embodiment 1

[0047] The preparation method of the fluorenone compound of following structural formula:

[0048]

[0049] In the 50mL Shrek tube, add substrate fluorene 166mg (1mmol), the amount of copper chloride dihydrate added is based on the molar weight of Cu, and the addition of copper chloride dihydrate is 5% of the substrate molar weight, specifically 8.5mg, add the molar amount of ligand L1 is 5% of the substrate molar amount, specifically 25mg, add 40mg (1eq.) of sodium hydroxide and 5mL of water, add magnetons, and place in an oil bath at 40°C under air conditions Stir the reaction for 4 hours, and filter the reaction solution after the reaction to obtain 175 mg of the target product with a yield of 97%. Target product characterization data: Yellow solid.(PE / DCM=10:1as eluent).mp 79-81℃. 1 H NMR (400MHz, CDCl 3 )δ=7.64(d, J=7.3Hz, 2H), 7.51-7.43(m, 4H), 7.30-7.24(m, 2H). 13 C NMR (100MHz, CDCl 3 )δ=193.93, 144.43, 134.69, 134.15, 129.08, 124.30, 120.32. LRMS (EI): m / z calcd ...

Embodiment 2

[0051] The preparation method of the fluorenone compound of following structural formula:

[0052]

[0053] Add substrate 2-bromofluorene 244mg (1mmol) in the 50mL Shrek tube, the amount of ferric trichloride added is based on the molar weight of Fe, and the added amount of ferric trichloride is 10% of the substrate molar weight, specifically 3.2 mg, the molar amount of ligand L2 added is 10% of the substrate molar amount, specifically 5 mg, 168 mg (3 eq.) of potassium hydroxide and 1.8 mL of water were added, magnetons were added, oxygen was replaced by 0.1 MPa, the tube was sealed, 80 Stir and react in an oil bath at °C for 12 hours. After the reaction, the reaction solution is filtered and separated to obtain 232.5 mg of the target product with a yield of 90%. Yellow solid.(PE / DCM=10:1as eluent).mp 143-146℃. 1 H NMR (400MHz, CDCl 3 )δ=7.76(d,J=1.7Hz,1H),7.66(d,J=7.4Hz,1H),7.63-7.59(m,1H),7.52-7.48(m,2H),7.39(d,J =7.9Hz,1H),7.36-7.29(m,1H). 13 C NMR (100MHz, CDCl 3 )...

Embodiment 3

[0055] The preparation method of the fluorenone compound of following structural formula:

[0056]

[0057] Add substrate 2,7-dibromofluorene 320mg (1mmol) in 50mL Shrek tube, the amount of adding palladium acetate is based on the molar weight of Pb, the adding amount of palladium acetate is 0.05% of the substrate molar weight, specifically 0.12 mg, the molar amount of added ligand L1 is 0.05% of the substrate molar weight, specifically 0.6mg, add 3.26g (10eq.) of cesium carbonate and 18mL of water, add magnetons, replace oxygen with 0.5MPa, and place in an oil bath at 100°C The reaction was stirred for 16 hours. After the reaction, the reaction solution was filtered and separated to obtain 330 mg of the target product with a yield of 98%. Target product characterization data Yellow solid.(PE / DCM=10:1as eluent).mp203-205℃. 1 H NMR (400MHz, CDCl 3 )δ=7.68(d,J=1.8Hz,2H),7.57-7.52(m,2H),7.30(d,J=7.9Hz,2H). 13 C NMR (100MHz, CDCl 3 )δ=189.93, 141.23, 136.45, 134.23, 126.82,...

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Abstract

The present invention aims at the technical problems of organic solvent pollution and generation of by-products in the method for synthesizing fluorenone compounds in the prior art, and provides a method for synthesizing fluorenone compounds by oxidation of molecular oxygen in the water phase, using fluorenone compounds as the base and disperse it in an alkaline aqueous solution, under the conditions of 40°C-120°C and the presence of oxygen, use a water-soluble transition metal complex as a catalyst, stir and react to obtain fluorenone compounds; the present invention uses molecular oxygen as an oxidant, Using water as a solvent avoids the use of organic solvents, and there is no problem of generating various by-products due to peroxidation.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fluorenone compounds, and in particular relates to a method for synthesizing fluorenone compounds by oxidation of molecular oxygen in a water phase. Background technique [0002] Fluorenone compounds are important fine chemical raw materials, which are widely used in dyes, medicines, and pesticides. For example, bisphenol fluorene synthesized from fluorenone is often used as a functional polymer material because of its unique Cardo ring skeleton structure, while fluorenyl epoxy resin has excellent moisture resistance, mechanical properties, dielectric properties, Comprehensive properties such as chemical resistance. Fluorenone compounds can also be used as pharmaceutical intermediates, mainly used in the synthesis of sympathetic nerve inhibitors, antispasmodic agents, anti-cancer and anti-tuberculosis drugs, etc., for example, 2-hydroxyaminoacetyl fluorenone is an antispasmodic A number of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/643C07C49/693C07C49/675C07C225/22C07C205/45C07C65/36C07C49/788C07C45/36C07C221/00C07C201/12C07C51/373
CPCC07C49/643C07C49/693C07C49/675C07C225/22C07C205/45C07C65/36C07C49/788C07C2603/18
Inventor 袁冰芯李恒李龙甲
Owner ZHENGZHOU UNIV
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