Preparation method of trifluoromethyl carbonyl compound
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A technology of compound and synthesis method, which is applied in the field of trifluoromethyl-containing organic compounds, and can solve the problems of low environmental pollution and the like
Inactive Publication Date: 2014-03-26
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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[0007] The present invention aims at the deficiencies of the existing synthesis methods of such fluorine-containing compounds, and provides a new synthesis method of trifluoromethyl carbonyl compounds. The carbonyl compounds include carboxylic acids, ketones and ester compounds. The catalysts and raw materials used are cheap and easy to obtain, and the reaction conditions are mild. The phenomenon of β-defluorination is effectively avoided during the reaction process. The environmental pollution is small, the yield is high, and the separation is simple. It conforms to the concept of green chemistry and has a wide range of industrial application prospects. , in addition, this method is also a new method of introducing single or multiple trifluoromethyl groups into the molecular structure with high efficiency and high atom economy, and it also effectively avoids the occurrence of metal catalysis when metal catalysis is used. Remaining general problem, the structural formula of the trifluoromethyl carbonyl-containing compound is:
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Embodiment 1
[0035] In a 10ml reaction tube, add 2-(trifluoromethyl)-3,3,3-trifluoropropionic acid methyl ester (0.2mmol), then add 2-dicyclohexylphosphine-2,4,6-triiso Propyl biphenyl (X-PHOS) (0.02mmol), then add 1mL N,N-dimethylformamide, and finally add phenyl vinyl ketone (0.6mmol), stir the reaction at 30°C for 1h, the reaction is complete, The conversion rate of 2-(trifluoromethyl)-3,3,3-trifluoropropionic acid methyl ester is 100% and the yield of fluorine spectrum is 99%. The product is obtained by column chromatography with an isolated yield of 95%. , the product structure and analysis data are as follows:
[0036] 5-Phenyl-2,2-bis(trifluoromethyl)-5-oxopentanoic acid methyl ester, 1 H NMR (300MHz, CDCl 3 )δ7.95(d,J=7.8Hz,2H),7.59(t,J=7.2Hz,1H),7.48(t,J=7.2Hz,2H),3.91(s,3H),3.14(t, J=7.8Hz,2H),2.65(t,J=7.8Hz,2H); 19 F NMR (282MHz, CDCl 3 )δ-66.2; HRMS (ESI) calcd for C 14 h 12 f 6 o 3 Na[M+Na] + 365.0581found 365.0582.
Embodiment 2~12
[0038] Similar to Example 1, X-PHOS was selected as the catalyst, methyl 2-(trifluoromethyl)-3,3,3-trifluoropropionate (0.2 mmol) was used as the reaction raw material, the solvent DMF1mL was added, and different substituted Phenyl vinyl ketones were reacted using the same analytical means as in Example 1. The reaction conditions and results are shown in Table 1.
[0039] Table 1
[0040]
[0041] Table 1
[0042]
Embodiment 2
[0043] The product structure and analysis data of embodiment 2 are as follows:
[0044] Methyl 5-(4-chlorophenyl)-2,2-bis(trifluoromethyl)-5-oxopentanoate, 1 H NMR (300MHz, CDCl 3 )δ7.89(d,J=8.4Hz,2H),7.46(d,J=8.4Hz,2H),3.92(s,3H),3.11(t,J=7.8Hz,2H),2.63(t, J=7.8Hz,2H); 19 F NMR (282MHz, CDCl 3 )δ-66.2; HRMS (EI) calcd for C 14 h 11 CIF 6 o 3 [M] + 376.0306 found 376.0301.
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Abstract
The invention discloses a preparation method of a trifluoromethyl carbonyl compound. The preparation method is characterized in that organic micromolecule phosphine is adopted to catalyze a fluorine-containing material and alpha, beta-unsaturated compounds to generate michael addition reaction, wherein a beta defluorination phenomenon is effectively avoided in the reaction process; moreover, compared with the existing synthetic method, the materials and the catalyst are cheap and easily available, reaction conditions are gentle and easy to control, the usage amount of the catalyst is less, post-treatment is simple, yield is high, application prospect is wide; meanwhile, carboxylic compounds containing alpha- trifluoromethyl also can be directly prepared after further hydrolysis of the alpha- trifluoromethyl ether compounds.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for catalyzing and synthesizing a class of trifluoromethyl-containing organic compounds that can be widely used in the fields of agricultural medicine and the like with an organic small molecule phosphine. Background technique [0002] Due to the small atomic radius and high electronegativity of fluorine atoms, fluorine-containing compounds have very unique properties in many fields, such as fluorine-containing medicine Lipitor, fluorine-containing triketones, fluorine-containing pyrazole amides, Fluoromethoxyacrylates have been widely used in the field of agricultural medicine due to their good biological activity. Nowadays, fluorine-containing compounds have a unique position in the fields of agricultural medicine and materials. [0003] The research on the methodology of synthesizing various fluorine-containing compounds has always been a hot issu...
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