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Trifluoromethylation method for biphenylyl olefin compound

A technology of compounds and synthetic methods, applied in chemical instruments and methods, organic chemistry, halogenated hydrocarbon preparation, etc., can solve the problems of low material conversion rate and long reaction time, and achieve good application prospects and industrial production potential. Effect

Inactive Publication Date: 2015-11-11
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] As mentioned above, although a variety of methods for trifluoromethylation reactions have been reported in the prior art, these reactions still have some drawbacks, such as the use of the highly toxic reagent SF 4 , or the conversion rate of the material is not high, or the reaction time is long, etc., resulting in many inconveniences in the industrial application of these methods

Method used

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  • Trifluoromethylation method for biphenylyl olefin compound
  • Trifluoromethylation method for biphenylyl olefin compound
  • Trifluoromethylation method for biphenylyl olefin compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Under the protection of nitrogen atmosphere, to an appropriate amount of organic solvent (a mixture of polyethylene glycol and 15-crown-5 with a volume ratio of 1:0.2) at room temperature, 100mmol of the compound of the above formula (I) and 250mmol of the above formula (II) ) Compound, 5mmol catalyst (1.25mmolPd(dba) 2 And 3.75mmol ytterbium trifluoromethanesulfonate), 10mmol oxidant silver acetate and 20mmol N-n-butyl-N-methylpiperidine bis(trifluoromethanesulfonyl)imide salt, and then heated to 50℃ , And the reaction was stirred at this temperature for 10 hours.

[0044] After the reaction is complete, filter, adjust the pH of the filtrate to neutral, then wash with saturated sodium bicarbonate aqueous solution, add dichloromethane for extraction, separate the organic phase, dry with anhydrous sodium sulfate, concentrate under reduced pressure, and leave the residue After 200-300 mesh silica gel column chromatography, using a mixture of petroleum ether and acetone in a ...

Embodiment 2

[0046] Under the protection of a nitrogen atmosphere, to an appropriate amount of organic solvent (a mixture of polyethylene glycol and 15-crown-5 with a volume ratio of 1:0.2) at room temperature, 100mmol of the compound of the above formula (I) and 200mmol of the above formula (II) ) Compound, 7mmol catalyst (2mmolPd(dba) 2 And 5mmol ytterbium trifluoromethanesulfonate), 15mmol oxidizer silver acetate and 25mmol accelerator N-n-butyl-N-methylpiperidine bis(trifluoromethanesulfonyl)imide salt, and then heated to 60°C, The reaction was stirred at this temperature for 8 hours.

[0047] After the reaction is complete, filter, adjust the pH of the filtrate to neutral, then wash with saturated sodium bicarbonate aqueous solution, add dichloromethane for extraction, separate the organic phase, dry with anhydrous sodium sulfate, concentrate under reduced pressure, and leave the residue After 200-300 mesh silica gel column chromatography, using a mixture of petroleum ether and acetone w...

Embodiment 3

[0049] Under the protection of nitrogen atmosphere, to an appropriate amount of organic solvent (a mixture of polyethylene glycol and 15-crown-5 with a volume ratio of 1:0.2) at room temperature, 100mmol of the compound of the above formula (I) and 250mmol of the above formula (II) ) Compound, 9mmol catalyst (being 3mmolPd(dba) 2 And 6mmol ytterbium trifluoromethanesulfonate), 12mmol oxidizer silver acetate and 30mmol accelerator N-n-butyl-N-methylpiperidine bis(trifluoromethanesulfonyl)imide salt, and then heated to 70°C, The reaction was stirred at this temperature for 6 hours.

[0050] After the reaction is complete, filter, adjust the pH of the filtrate to neutral, then wash with saturated sodium bicarbonate aqueous solution, add dichloromethane for extraction, separate the organic phase, dry with anhydrous sodium sulfate, concentrate under reduced pressure, and leave the residue After 200-300 mesh silica gel column chromatography, using a mixture of petroleum ether and aceto...

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Abstract

The invention relates to a synthetic method of a compound shown in a formula (III), wherein the formula (III) is shown in the description. The method comprises: carrying out a reaction on a compound shown in a formula (I) and a compound shown in a formula (II) in a nitrogen condition and in an organic solvent in the presence of a double-component catalyst, an oxidizing agent and an accelerant so as to obtain the compound shown in the formula (III), wherein the formula (III) is shown in the description, and R is H, C1-C6 alkyl, C1-C6 alkoxyl or halogen. The method can be used for obtaining the target product with a high yield through comprehensive selection and coordination of the catalyst, the accelerant, the organic solvent and the like, and has a good application prospect and industrial potential productivity in the field of organic chemical synthesis.

Description

Technical field [0001] The invention relates to a 1,2-bis(trifluoromethyl) reaction method for olefins, and more particularly to a method for trifluoromethylation of biphenyl olefin compounds, and belongs to the field of organic intermediate synthesis. Background technique [0002] Among the organic active groups, trifluoromethyl is a very useful structural modification functional group, which has the ability to improve the lipophilicity, metabolic activity and bioavailability of the compound, so it has received extensive attention in various fields. [0003] Many reaction methods related to trifluoromethylation modification have been reported in the prior art, such as: [0004] As early as 20 years ago, Yu.M.Pustovit et al. ("ReactionsofcycloalkanecarboxylicacidswithSF4.I.FluorinationofcyclopropanepolycarboxylicacidswithSF 4 ", JournalofFluorineChemistry, 1994, 69, 225-229) reported a use of SF 4 Reaction process of fluorinated cycloalkane carboxylic acid. [0005] Gary A. Molander e...

Claims

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Application Information

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IPC IPC(8): C07C22/08C07C17/32
Inventor 翁月林
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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