Synthetic method of 3,4,5-trifluoro-2'-nitrobiphenyl
A technology of nitrobiphenyl and synthesis method, which is applied in the fields of chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of catalysts, difficulty in large-scale application, and lack of quality, and achieve short synthesis steps , no three wastes discharge, simple treatment effect
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[0042] The present invention also provides a synthetic method of 3,4,5-trifluoro-2'-nitrobiphenyl, characterized in that, comprising:
[0043] Step 1: Dissolving the raw materials 3,4,5-trifluorophenylboronic acid and o-nitro-substituted benzene in a solvent, and adding a catalyst and an acid-binding agent;
[0044] Step 2: stirring reaction, to end;
[0045] Step 3: washing with water and extracting to obtain an organic phase;
[0046] Step 4: Concentrate and recrystallize to obtain 3,4,5-trifluoro-2'-nitrobiphenyl.
[0047] According to a preferred embodiment of the second aspect of the present invention, in the step 1:
[0048] Wherein, the solvent is selected from any one of protic solvents and aprotic solvents: the protic solvents include methanol, ethanol, propanol, isopropanol, water, formic acid and acetic acid, preferably methanol; Aprotic solvents include N,N-dimethylformamide, acetone, ethyl acetate, dichloromethane, ether, carbon tetrachloride, toluene, benzene,...
Embodiment 1
[0069] Embodiment 1 -- about the screening of catalyst
[0070] 1. Synthetic route:
[0071]
[0072] 2, synthetic method (carry out according to table 1):
[0073] Step 1: Set up 4 reactions, dissolve the raw materials 3,4,5-trifluorophenylboronic acid and o-chloronitrobenzene in the solvent DMF, add the acid-binding agent triethylamine, and add the catalyst PtCl respectively 2 , Pd(OAc) 2 , Pd(PPh 3 ) 4 , Ms-Pd, the addition amount is 0.5%;
[0074] Step 2: Stir the reaction at 30°C, and stop the reaction after the liquid phase traces the reaction of the raw materials;
[0075] Step 3: Recover the solvent and catalyst, and the crude product is washed with water and extracted to obtain an organic phase;
[0076] Step 4: Concentrate and recrystallize from n-hexane to obtain 24.0 g of 3,4,5-trifluoro-2'-nitrobiphenyl as the best result, a light yellow crystalline solid with a melting point of 78.1-78.3°C and a liquid phase content of 97% . 1 H NMR (400MHz, CDCl 3 )δ...
Embodiment 2
[0080] Embodiment 2——Screening about-X
[0081] 1. Synthetic route:
[0082]
[0083] 2, synthetic method (carry out according to table 2):
[0084] Step 1: Set up 3 reactions, respectively dissolve the raw materials 3,4,5-trifluorophenylboronic acid and 3 kinds of o-nitro-substituted benzenes in the solvent methanol, and add the acid-binding agent sodium bicarbonate and the catalyst PdCl 2 , the addition amount is 0.5%;
[0085] Step 2: Stir the reaction at 40°C, and stop the reaction after the liquid phase traces the reaction of the raw materials;
[0086] Step 3: Recover the solvent and catalyst, and the crude product is washed with water and extracted to obtain an organic phase;
[0087] Step 4: Concentration to obtain 3,4,5-trifluoro-2'-nitrobiphenyl.
[0088] 3. Results:
[0089] Table 2: Test results for -X screening
[0090] Numbering -X catalyst Acid Binder temperature(℃) solvent yield 1 -Cl PdCl 2
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