A kind of fluorine-containing alkyne alcohol compound and its synthesis method

A synthesis method and compound technology are applied in the field of fluorine-containing alkynol compounds and their novel synthesis, which can solve problems such as environmental pollution, and achieve the effects of simple and convenient operation, environment-friendly synthesis method and high yield.

Inactive Publication Date: 2016-08-24
HANGZHOU FST PHARMA
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  • Abstract
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Problems solved by technology

Motoki et al. using catalyst CuO t Bu and diphosphine or dinitrogen ligands achieve direct alkynylation of trifluoromethyl ketones, and their reactions are carried out in tetrahydrofuran or toluene (OrganicLetters, 2007, 9(16): 2997-3000), but the use of organic solvents is harmful to polluting the environment, causing environmental problems

Method used

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  • A kind of fluorine-containing alkyne alcohol compound and its synthesis method
  • A kind of fluorine-containing alkyne alcohol compound and its synthesis method
  • A kind of fluorine-containing alkyne alcohol compound and its synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 0.8706 g (5 mmol) of trifluoroacetophenone, 1.65 mL (15 mmol) of phenylacetylene, and 0.0425 g (0.25 mmol Ag + ) as the catalyst, triethylamine 0.14mL (1 mmol), triphenylphosphine 0.0656 g (0.25 mmol), water 20 mL, stirred at 10°C for 15 h. After the reaction was complete, it was extracted with ethyl acetate, and the organic phase was dried and separated by column chromatography to obtain a fluorine-containing alkynol compound (petroleum ether: ethyl acetate = 25:1). The product was a light yellow liquid with a yield of 98%.

[0030] The physicochemical index of this product: 1 H-NMR (400 MHz, CDCl 3 ) : δ=7.71 (s, 2H), 7.40 (d, J=7.6Hz, 2H), 7.30 - 7.29 (m, 3H), 7.26 - 7.19 (m, 3H), 3.43 (s, 1H); 13 C-NMR (CDCl 3 , 100 MHz): 135.5, 132.2, 129.6, 128.6, 128.4, 127.3, 125.0, 122.1,121.1, 88.1, 84.6, 73.6, 73.3; IR (v max / cm -1 ): 3545.8, 3064.7, 2233.7, 1599.7, 1490.9, 1355.1, 1186.4, 1066.7, 933.3, 757.6, 691.0.

Embodiment 2

[0032]Add 0.8706 g (5 mmol) of trifluoroacetophenone, 1.9824 g (15 mmol) of p-methoxyphenylacetylene, 0.0083 g (0.05 mmol) of silver acetate, and 0.21 mL (2 mmol), triphenylphosphine 0.1311 g (0.5 mmol), water 10 mL as solvent, and stirred at 25°C for 15 h. After the reaction was complete, it was extracted with ethyl acetate, and the organic phase was dried and separated by column chromatography to obtain a fluorine-containing alkynol compound (petroleum ether: ethyl acetate = 25:1). The product was a light yellow liquid with a yield of 92%.

[0033] The physicochemical index of this product: 1 H-NMR (400 MHz, CDCl 3 ) : δ=7.81 (d, J=7.6Hz, 2H),7.46 - 7.42 (m, 5H), 6.87 (d, J=8.8Hz, 2H), 3.82 (s, 3H), 3.18 (s, 1H) ; 13 C-NMR (CDCl 3 IR (v max / cm -1 ): 3431.1, 2960.4, 2841.5, 2231.0, 1605.9, 1510.8, 1452.1, 1294.6, 1249.2, 1173.3, 1066.0, 832.3, 707.1.

Embodiment 3

[0035] Under an argon atmosphere, 3.1284 g (15 mmol) of p-chlorotrifluoroacetophenone, 1.8018 g (15 mmol) of p-fluorophenylacetylene, 0.3806 g (3 mmol) of silver fluoride, and 0.73 mL (9 mmol) of pyridine were added to the reaction system. mmol), 0.7923 g (1.5 mmol) of triphenylphosphine substituted by binaphthol derivatives (structural formula (III)), 10 mL of water, heated and stirred at 100°C for 8 h. After the reaction is complete, cool to room temperature, extract with ethyl acetate, and obtain the fluorine-containing alkynol compound (petroleum ether: ethyl acetate=25:1) by column chromatography after the organic phase is dried. The product is a light yellow liquid, and the yield is 98%.

[0036] (III)

[0037] The physicochemical index of this product: 1 H-NMR (400 MHz, CDCl 3 ) : δ=7.77 (d, J=8.4Hz, 2H),7.54 - 7.51 (m, 2H), 7.42 (d, J=8.8Hz, 2H), 7.08 (t, J=8.4Hz, 2H), 3.82 (s,1H); 13 C-NMR (CDCl 3 , 100 MHz): 164.6, 162.1, 135.7, 134.2, 134.1, 133.9,128.7, 12...

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Abstract

The invention relates to the field of fine chemistry, and provides a fluorine-containing alkynol compound and a synthesis method thereof in order to solve the problem of environmental pollution and realize green construction of a fluorine-containing organic compound. The method comprises the following steps: under inert gas protection, adding trifluoroacetophenone and alkyne-terminated compound into a dried container; in the joint action of a catalyst, organic base and phosphine ligand, heating to 10-100 DEG C by taking water as a solvent; stirring for 8-24 hours, and then cooling to room temperature; extracting with ethyl acetate; drying the organic phase, and separating and purifying through silica-gel column chromatography to obtain the fluorine-containing alkynol compound. The method provided by the invention can be performed in a water phase, reduces the environmental pollution, is an environment-friendly green synthesis method conforming to the development of modern chemistry, and has an important value in industrial application; meanwhile, the synthesis method provided by the invention is simple and convenient to operate, the reaction conditions are mild, and the yield is relatively high.

Description

technical field [0001] The invention relates to the field of fine chemical industry, in particular to a fluorine-containing alkynol compound with multiple functional groups and a novel synthesis method thereof. Background technique [0002] Since the advent of freon in the early 1930s, organic fluorine chemistry and its fluorine-containing organic compounds have been showing a vigorous development trend, showing great application value in various fields. Because the introduction of fluorine atoms leads to unique physical and chemical properties and physiological activities of organic compounds, it is used in many cutting-edge technologies such as atomic energy industry, rockets, aerospace, etc., as well as some major industrial projects such as fuel cell technology, medicine, and pesticides. Fluorine-containing compounds have been widely and deeply researched and applied, especially in recent years, the development of fluorine-containing fine chemical industry is in the asce...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/48C07C29/44C07C43/23C07C41/30
CPCC07C29/42C07C33/48
Inventor 杨科芳徐利文王虎郑战江李莉蒋剑雄来国桥邓元盛春荠蒋可志瞿志荣
Owner HANGZHOU FST PHARMA
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