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A kind of preparation method and application of fluoroolefin

A fluoroolefin and reaction tube technology, which is applied in the field of preparation of fluoroolefins, can solve the problems of insufficient selectivity, complex catalytic system, low reaction activity, etc., and achieves high selectivity, simple catalytic system and wide reaction range. Effect

Active Publication Date: 2022-04-15
YUNNAN MINZU UNIV
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  • Abstract
  • Description
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Problems solved by technology

[0012] To sum up, the problems existing in the prior art are: the current synthesis of fluoroolefins mainly relies on metal catalysis, the cost is high, the catalytic system is complicated, the operation is complicated, the selectivity is not high enough, and it will cause environmental pollution
[0013] Difficulty in solving the above-mentioned technical problems: no transition metal is required, there are problems of low reactivity and low yield, the reaction is a series reaction of two-step reactions, and there may be many side reactions, resulting in low yield

Method used

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  • A kind of preparation method and application of fluoroolefin
  • A kind of preparation method and application of fluoroolefin
  • A kind of preparation method and application of fluoroolefin

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preparation example Construction

[0043] The preparation method of the fluoroolefin provided by the embodiment of the present invention comprises:

[0044] Under the catalysis of light, the difluoroalkylation-defluorination reaction using ethyl difluoroiodoacetate as the fluorine source, and the high stereoselective synthesis of fluoroalkenes by ketonization of aryl benzyl.

[0045] Such as figure 1 As shown, the preparation method of the fluoroolefin provided by the embodiment of the present invention comprises the following steps:

[0046] S101, in the glove box, add the accurately weighed ketone into the Schneck reaction tube with a stirring bar, dissolve the ketone in the solvent, put on a rubber stopper and take it out of the glove box.

[0047] S102. Stir the reaction tube at a certain temperature, draw a certain amount of alkali with a syringe, and add it to the reaction tube; turn on the light source after 5-10 minutes.

[0048] S103, adding ethyl difluoroiodoacetate into the reaction tube, reacting...

Embodiment 1

[0057]

[0058] In the glove box, accurately weigh 2-phenylacetophenone (0.2 mmol) and add it to a Schneck reaction tube with a stirring bar, dissolve it in tetrahydrofuran, put on a rubber stopper and remove it from the glove box. The reaction tube was stirred at -20° C., and then sodium bis(trimethylsilyl)amide (0.32 mmol) was added to the reaction tube with a syringe. Turn on the LED blue light after 5-10 minutes. Subsequently, ethyl difluoroiodoacetate (0.4 mmol) was added into the reaction tube, and reacted for two hours, and the reaction progress was monitored by TLC and GC-MS. After the reaction was over, the reaction tube was taken out, and the reaction solution was removed under reduced pressure using a rotary evaporator to remove volatile solvents, and ethyl acetate / petroleum ether was used as eluent, and purified by column chromatography to obtain monofluoroolefins (76% yield, E / Z=97:3).

[0059]1H NMR (400MHz, CDCl3) δ8.05-7.94 (m, 2H), 7.63-7.49 (m, 3H), 7.44...

Embodiment 2

[0061]

[0062] In the glove box, accurately weigh 2-(4-methoxyphenyl)acetophenone (0.2mmol) and add it to a Schneck reaction tube with a stirring bar, dissolve it in tetrahydrofuran, plug it with a rubber stopper and remove it. glove box. The reaction tube was stirred at -20° C., and then sodium bis(trimethylsilyl)amide (0.32 mmol) was added to the reaction tube with a syringe. Turn on the LED blue light after 5-10 minutes. Subsequently, ethyl difluoroiodoacetate (0.4 mmol) was added into the reaction tube, and reacted for two hours, and the reaction progress was monitored by TLC and GC-MS. After the reaction was over, the reaction tube was taken out, and the reaction solution was removed under reduced pressure using a rotary evaporator to remove volatile solvents, and ethyl acetate / petroleum ether was used as eluent, and purified by column chromatography to obtain monofluoroolefins (67% yield, E / Z=98:2).

[0063] 1 H NMR (400MHz, CDCl3) δ8.03-7.92 (m, 2H), 7.58-7.48 (...

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Abstract

The invention belongs to the technical field of organic fluorides, and discloses a preparation method and application of fluoroolefins. Under the catalysis of light, difluoroalkylation-defluorination reaction using ethyl difluoroiodoacetate as a fluorine source, Highly stereoselective synthesis of fluoroalkenes by ketolation of arylbenzyls. The invention uses ethyl difluoroiodoacetate as a fluorine source to prepare monofluoroolefin compounds with high selectivity, can greatly reduce production costs, and has remarkable social and economic benefits. The catalyst system of the invention is simple, easy to operate and good in selectivity. The invention adopts a photocatalysis strategy, which is more green and environment-friendly than the existing metal catalysis. The synthesis method of the present invention uses ethyl difluoroiodoacetate as the difluoroalkylation-defluorination reaction of the fluorine source, has high regioselectivity, mild reaction conditions, wide reaction range, and can efficiently synthesize fluorinated Olefins can realize scientific and technological applications, promote the development of medicine and meet the needs of scientific research.

Description

technical field [0001] The invention belongs to the technical field of organic fluorides, in particular to a preparation method and application of fluoroolefins. Background technique [0002] Currently, the closest prior art: organofluorine compounds are widely used in medicine, pesticides and special materials due to their unique chemical and physical properties. Monofluoroolefins are an important class of fluorinated compounds with potential applications in materials science and synthetic organic chemistry. Currently, 20% of pharmaceuticals and 30%-40% of agricultural chemicals on the market contain at least one fluorine atom in their structure. In medicinal chemistry, they may serve as isoelectronics of amide bonds and analogs of enols, as follows: [0003] [0004] In addition, monofluoroalkenes, as an ideal peptide bond isomer in medicinal chemistry, widely exist in many bioactive molecules with different pharmacological activities, and can exist in DPP IV inhibito...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/343C07C69/738
CPCC07C67/343C07C69/738
Inventor 周永云樊保敏陈景超和振秀樊瑞峰孙蔚青李康葵
Owner YUNNAN MINZU UNIV
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