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Synthetic method for cyanophenyl compound

A synthesis method and compound technology, applied in the preparation of organic compounds, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc. The effect of good industrial production prospects and potential

Inactive Publication Date: 2016-10-12
刘利楠
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] As mentioned above, multiple synthetic methods for the synthesis of aryl cyano groups have been disclosed in the prior art, but these methods still cannot meet the needs of organic synthesis and drug synthesis in relation to the diversity of reactions. etc. also need to be improved

Method used

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  • Synthetic method for cyanophenyl compound
  • Synthetic method for cyanophenyl compound
  • Synthetic method for cyanophenyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] At room temperature, in an appropriate amount of organic solvent PEG-200, add 100mmol of the above formula (I) compound, 150mmol of the above formula (II) compound, 20mmol of catalyst (5mmol bis(1,5-cyclooctadiene) iridium tetrafluoroborate and 15mmol AgSbF 6 mixture), 20mmol ligand L1 and 15mmol auxiliary agent (a mixture of 7.5mmol lanthanum trifluoromethanesulfonate and 7.5mmol cerium ammonium nitrate), then the temperature was raised to 80°C, and the reaction was stirred at this temperature for 12 hours;

[0036] After the reaction is over, filter the reaction system while it is hot, add an equal volume of saturated sodium carbonate aqueous solution to the filtrate, shake fully, then add ethyl acetate to extract 2-3 times, combine the organic phases, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure , the residue was separated by 300-400 mesh silica gel column chromatography, and eluted with a mixture of acetone and petroleum e...

Embodiment 2

[0039]

[0040] At room temperature, in an appropriate amount of organic solvent PEG-200, add 100mmol of the above formula (I) compound, 250mmol of the above formula (II) compound, 10mmol of catalyst (2mmol bis(1,5-cyclooctadiene) iridium tetrafluoroborate and 8 mmol AgSbF 6 mixture), 30mmol ligand L1 and 8mmol auxiliary agent (a mixture of 4mmol lanthanum trifluoromethanesulfonate and 4mmol cerium ammonium nitrate), then the temperature was raised to 100°C, and the reaction was stirred at this temperature for 8 hours;

[0041]After the reaction is over, filter the reaction system while it is hot, add an equal volume of saturated sodium carbonate aqueous solution to the filtrate, shake fully, then add ethyl acetate to extract 2-3 times, combine the organic phases, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure , the residue was separated by 300-400 mesh silica gel column chromatography, and eluted with a mixture of acetone and petroleum ether a...

Embodiment 3

[0044]

[0045] At room temperature, in an appropriate amount of organic solvent PEG-200, add 100mmol of the above formula (I) compound, 200mmol of the above formula (II) compound, 15mmol of catalyst (3.5mmol bis(1,5-cyclooctadiene) iridium tetrafluoroborate with 11.5mmol AgSbF 6 mixture), 25mmol of ligand L1 and 12mmol of additives (a mixture of 6mmol of lanthanum trifluoromethanesulfonate and 6mmol of cerium ammonium nitrate), then the temperature was raised to 90°C, and the reaction was stirred at this temperature for 10 hours;

[0046] After the reaction is over, filter the reaction system while it is hot, add an equal volume of saturated sodium carbonate aqueous solution to the filtrate, shake fully, then add ethyl acetate to extract 2-3 times, combine the organic phases, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure , the residue was separated by 300-400 mesh silica gel column chromatography, and eluted with a mixture of acetone and petr...

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Abstract

The invention relates to a synthetic method for a cyanophenyl compound. The method comprises the following steps: reacting a compound as shown in a formula (I) which is described in the specification with a compound (i.e., N-cyano-N-phenyl-p-toluenesulfonamide) as shown in a formula (II) which is described in the specification in an organic solvent in the presence of a catalyst, ligand and an auxiliary agent, and carrying out treatment after completion of the reaction so as to obtain a compound as shown in a formula (III) which is described in the specification. In the formula (III), R is selected from H, C1-6 alkyl groups, C1-6 alkyloxy groups, a nitro group, a cyano group or a phenyl group. The method employs cooperation of a specific reaction substrate, the catalyst, the ligand, the auxiliary agent and the organic solvent to realize high yield of the cyanophenyl compound; so a novel synthetic method for the cyanophenyl compound is provided, and the method has good industrial production prospect and potential.

Description

technical field [0001] The invention relates to a method for synthesizing cyano compounds, more particularly to a method for synthesizing aromatic cyano compounds, and belongs to the technical field of organic chemical synthesis. Background technique [0002] The aryl cyano group is an important structural unit of many drug molecules, material molecules and dye molecules. It can also be used as a synthetic intermediate of amines, imines and ketones, and has a wide range of uses. Therefore, the development of efficient synthesis methods for aromatic cyano compounds has become one of the hot issues that researchers have paid close attention to. [0003] As we all know, there have been a variety of methods for synthesizing aromatic cyano compounds in the prior art, among which the more classic types include Sandmeyer reaction, Rosenmund-vonBraun reaction, etc.; Synthesis of cyano compounds such as: [0004] Dinesh N. Sawant et al. ("Cyanides-Free Cyanation of Aryl Halides usi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/00C07C255/50C07C255/51C07C255/54B01J31/26
CPCC07C253/00B01J31/26B01J2531/0258B01J2531/827C07C255/50C07C255/51C07C255/54
Inventor 刘利楠谢文强
Owner 刘利楠
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