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Ruthenium catalyst and application thereof

A ruthenium catalyst and catalyst technology, applied in catalytic reactions, physical/chemical process catalysts, ruthenium organic compounds, etc., to achieve mild reaction conditions, good stability, and less by-products

Active Publication Date: 2021-12-17
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is reported in the literature (Wei Li, Qi-Lin Zhou et al, Green Chemistry, 2014, 4081-4085) that using ruthenium catalysts for hydrogenation, the reaction time reaches several hours to tens of hours, the hydrogen pressure needs to be 50 or more atmospheric pressure, and the reaction temperature is also low. It should be higher than 100 degrees Celsius; only 1-2 fluorine atoms are substituted on the benzene ring, and the fluorobenzoic acid ester can only be methyl fluorobenzoate; the reduction of benzoic acid esters substituted by more than 2 fluorine atoms no report

Method used

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  • Ruthenium catalyst and application thereof
  • Ruthenium catalyst and application thereof
  • Ruthenium catalyst and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Reaction formula

[0044]

[0045] The 10mmol2- diphenylphosphino - benzaldehyde was added dry three neck round bottom flask was added 100mL of anhydrous methanol, was added 5 mmol of 1,2-cyclohexanediamine. It was stirred under nitrogen at room temperature for 12 hours, heated under reflux for 3 hours under ice-cooling to 0 ℃. Suction filtration, washed with cold ethanol 5mL, 10 mL each of ether washed three times. A yellow solid is phosphorus, nitrogen ligand, a yield of 81.7%.

Embodiment 2

[0047] Reaction formula

[0048]

[0049] Under nitrogen, after the two 5mmol tetrakis (dimethylsulfoxide) ruthenium and dried 40mL N, N- dimethylformamide was added to the dried round bottom flask, was added with stirring 5mmol phosphorus, nitrogen Ligand. It was heated under stirring to a solvent (N, N- dimethylformamide) at reflux for 3 hours. The solvent was distilled off under reduced pressure to about 30mL, the residue was cooled to room temperature, filtered off with suction, washed with cold anhydrous methanol for 3 times. After drying in vacuo to give a red catalyst, a yield of 87.9%.

Embodiment 3

[0051] Reaction formula

[0052]

[0053] 10.65g 2,3,5,6- tetrafluoro added to 100mL autoclave of dimethyl terephthalate, 1.51 g of sodium boron hydride, 33.0 mg of the catalyst obtained in Example 2 above, 60 mL of tetrahydrofuran, 5 atm hydrogen gas is protected 100 ℃ heat the reaction was stirred for 5 hours. The reaction mixture was filtered, and the filtrate was distilled under reduced pressure the residue was chromatographed to give 2,3,5,6-tetrafluoro-4-hydroxymethyl - benzoic acid methyl ester, a yield of 86.9%.

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PUM

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Abstract

The invention relates to the field of pesticides and medicines, in particular to preparation of a ruthenium catalyst and application of the ruthenium catalyst in catalyzing reduction of polyfluorobenzoate into polyfluorobenzyl alcohol. The catalyst is shown in the formula I in the specification, and the catalyst can catalyze the reduction of polyfluorobenzoate into polyfluorobenzyl alcohol. The catalyst provided by the invention is simple to prepare, cheap and stable, is wide in application range when being applied to catalysis of pyrazole compounds and halogen-containing aromatic rings or heterocyclic rings, and is simple to prepare, high in yield and mild in reaction condition.

Description

Technical field [0001] The present invention relates to pesticide and pharmaceutical field, in particular ruthenium catalyst is prepared by the catalyzed reduction of a multi-fluorobenzoate multi-fluorophenyl methanol. Background technique [0002] Methanol is an important intermediate multi-fluorophenyl, having a unique structure, a derivative having distinctive biological activity, have an important role in medicine and pesticide. [0003] Multi-fluoro-benzoate was reduced to multi-fluorophenyl methanol is an important synthetic routes. Reported (Wei Li, Qi-Lin Zhou et al, Green Chemistry, 2014,4081-4085) hydrogenation using a ruthenium catalyst, the reaction time is several hours to several tens of hours, the hydrogen pressure needs to 50 or more atmospheres and the reaction temperature higher than 100 degrees Celsius; only 1-2 fluorine atoms substituted on the benzene ring, and fluoro benzoate is unique and can only be fluorobenzoate; more than two fluorine atoms substituted ...

Claims

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Application Information

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IPC IPC(8): B01J31/24B01J31/18C07F15/00C07C67/31C07C69/78C07C29/147C07C29/149C07C33/46
CPCB01J31/2409B01J31/189C07F15/0053C07C67/31C07C29/147C07C29/149B01J2531/821B01J2531/0252B01J2231/641C07C33/46C07C69/78
Inventor 姜鹏王嫱于海波杨浩
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD