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Method for synthesizing 3,4,5-trifluoro-2'-nitrobiphenyl

A technology of nitrobiphenyl and synthesis method, applied in chemical instruments and methods, preparation of organic compounds, molecular sieve catalysts, etc., can solve problems such as catalyst problems, lack of good quality, and difficulty in large-scale application, and achieves short synthesis steps. , No three wastes discharge, simple treatment effect

Active Publication Date: 2015-04-22
SHANGHAI SHENGNONG PESTICIDE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, the patent (PCT 2009156359) discloses a kind of 2,2-dimethyl-1,3-diphenylphosphinopropane (CAS: 80326-98-3) as raw material, PdCl 2 as a catalyst, and synthesize the above-mentioned biphenyl compound at high temperature and high pressure. However, the catalyst has no source of purchase, and in the process of replicating its synthesis method, good results cannot be obtained due to catalyst problems. Moreover, the synthesis environment High temperature and high pressure are required, so it is difficult to apply it on a large scale in factory production

Method used

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  • Method for synthesizing 3,4,5-trifluoro-2'-nitrobiphenyl

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preparation example Construction

[0042] The present invention also provides a method for synthesizing 3,4,5-trifluoro-2'-nitrobiphenyl, which is characterized in that it comprises:

[0043] Step 1: Dissolve raw materials 3,4,5-trifluorophenylboronic acid and o-nitro-substituted benzene in a solvent, and add a catalyst and an acid binding agent;

[0044] Step 2: Stir the reaction to the end;

[0045] Step 3: Wash with water and extract the 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 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, n-hexane, cyclohexane,...

Embodiment 1

[0069] Example 1-About the screening of catalysts

[0070] 1. Synthetic route:

[0071]

[0072] 2. Synthesis method (according to Table 1):

[0073] Step 1: Set up 4 reactions, dissolve raw materials 3,4,5-trifluorophenylboronic acid and o-chloronitrobenzene in solvent DMF, add acid binding agent triethylamine, and add 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 tracking raw material reaction is completed;

[0075] Step 3: Recover the solvent and catalyst, and the crude product is washed and extracted to obtain an organic phase;

[0076] Step 4: Concentrate and recrystallize from n-hexane to obtain 3,4,5-trifluoro-2'-nitrobiphenyl. The best result is 24.0g, light yellow crystalline solid, melting point 78.1-78.3℃, liquid content 97% . 1 H NMR(400MHz, CDCl 3 )δ8.00-8.05(m,2H),7.90-7.75(m,1H),7.67-7.55(m,1H),7.27-7.14(m,2H)ppm; 13C NMR(100MHz,CDCl3)δ1...

Embodiment 2

[0080] Example 2-Screening on -X

[0081] 1. Synthetic route:

[0082]

[0083] 2. Synthesis method (according to Table 2):

[0084] Step 1: Open 3 reactions, respectively dissolve raw materials 3,4,5-trifluorophenylboronic acid and 3 kinds of o-nitro-substituted benzene in solvent methanol, and add acid binding agent sodium bicarbonate and 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 tracking raw material reaction is completed;

[0086] Step 3: Recover the solvent and catalyst, and the crude product is washed and extracted to obtain an organic phase;

[0087] Step 4: Concentrate to obtain 3,4,5-trifluoro-2'-nitrobiphenyl.

[0088] 3. Results:

[0089] Table 2: Test results of -X screening

[0090] Numbering

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Abstract

The invention provides a method for synthesizing 3,4,5-trifluoro-2'-nitrobiphenyl; a synthetic route is as shown in the description, wherein -X represents a substituent group selected from one of -Cl, -Br, -I, COOH, -N2Cl and -N2HSO4. The method comprises the following steps of (1), dissolving the raw materials including 3,4,5-trifluorobenzeneboronic acid and ortho-nitro substituted benzene in a solvent, and adding a catalyst and an acid-binding agent; (2), reacting while stirring till finishing; (3), washing, and extracting to obtain an organic phase; and (4), concentrating, and recrystallizing to obtain 3,4,5-trifluoro-2'-nitrobiphenyl. According to the invention, the Ms-Pd catalyst having high catalytic activity is adopted; furthermore, multi-batch indiscriminate use can be realized; and the method is high in yield, high in product purity, convenient to postprocess and environment friendly.

Description

Technical field [0001] The present invention relates to an important intermediate for synthesizing fluoxazone, in particular to the synthesis of a functional group biphenyl compound, specifically a synthesis method of 3,4,5-trifluoro-2'-nitrobiphenyl. Background technique [0002] Functional group biphenyl compound, due to its own physical and chemical properties, is widely used directly or indirectly in the synthesis and preparation of drugs and pesticides. It is a very important bulk compound. The study of its synthesis method has important implications for the development of related fields. Significantly. [0003] Among them, 3,4,5-trifluoro-2'-nitrobiphenyl, as a functional group biphenyl compound, is an important intermediate in the field of fine chemicals, especially as a synthetic raw material for the insecticide fluroxypyr . Regarding 3,4,5-trifluoro-2'-nitrobiphenyl: its molecular formula is: C 12 H 6 F 3 NO 2 ; Chemical name: 3,4,5-Trifluoro-2'-nitrobiphenyl; English na...

Claims

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Application Information

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IPC IPC(8): C07C205/12C07C201/12B01J29/74
Inventor 叶振君韩海平王莲玉毕强黄凡张芝平旷东张洪玉吴清阳张忠明方燕
Owner SHANGHAI SHENGNONG PESTICIDE
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