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Synthesis method of biaryl compounds

A synthesis method and technology of aromatic compounds, which are applied in the preparation of organic compounds, carbon compound catalysts, chemical instruments and methods, etc., can solve the problems of unavailable catalysts, low reaction yields, and poor selectivity, and achieve green, safe, and safe synthesis reactions. The effect of shortening the reaction time and improving the synthesis efficiency

Inactive Publication Date: 2018-07-20
UNIV OF JINAN
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its synthesis process is complex, costly and atom-economical
[0004] In summary, although there are many reports on the synthesis methods of biaryl compounds in the prior art, there are still problems such as difficult access to catalysts, high catalyst prices, low reaction yields, poor selectivity, poor applicability, and complex synthesis processes.

Method used

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  • Synthesis method of biaryl compounds
  • Synthesis method of biaryl compounds
  • Synthesis method of biaryl compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] (1) Put 10mol% of diethylurea (0.02mmol), 0.6mmol of potassium tert-butoxide, 0.2mmol of p-iodoanisole and 2ml of benzene in a reaction tube, heat and stir for reaction, and the heating and stirring temperature is 120°C , The reaction time is 24h;.

[0049] (2) After the reaction is over, separate by column chromatography (the chromatographic column filler is 300-400 mesh column chromatography silica gel, and the eluent is: petroleum ether: ethyl acetate=100:0.5, v:v), the product can be obtained 4-Methoxybiphenyl, yield 94%. The structural characterization of the product is as figure 1 shown.

[0050] The structural characterization data of the product are as follows:

[0051] 1 H NMR (400MHz, CDCl 3 )δ7.59–7.54(m,4H),7.44(t,J=7.4Hz,2H),7.32(t,J=7.36Hz,1H),7.00(t,J=8.84Hz,2H),3.87( s,3H).MS(CI) Calcd for C 13 h 12 O:184; Found(M+H + ):185.

Embodiment 2

[0053] (1) Put 10mol% of diethylurea (0.02mmol), 0.6mmol of potassium tert-butoxide, 0.2mmol of m-iodoanisole and 2ml of benzene in a reaction tube, heat and stir for reaction, and the heating and stirring temperature is 120°C , The reaction time is 24h.

[0054] (2) After the reaction is over, separate by column chromatography (the chromatographic column filler is 300-400 mesh column chromatography silica gel, and the eluent is: petroleum ether: ethyl acetate=100:0.5, v:v), the product can be obtained 3-Methoxybiphenyl, yield 51%.

[0055] The structural characterization data of the product are as follows:

[0056] 1 H NMR (400MHz, CDCl 3 )δ7.64–7.61(m,2H),7.47(t,J=7.24Hz,2H),7.41–7.37(m,2H),7.23–7.16(m,2H),6.95–6.92(m,1H) ,3.89(s,3H).MS(CI) Calcd for C 13 h 12 O:184; Found(M+H + ):185.

Embodiment 3

[0058] (1) Put 10mol% of diethylurea (0.02mmol), 0.6mmol of potassium tert-butoxide, 0.2mmol of o-iodoanisole and 2ml of benzene in a reaction tube, heat and stir for reaction, and the heating and stirring temperature is 120°C , The reaction time is 24h.

[0059] (2) After the reaction is over, separate by column chromatography (the chromatographic column filler is 300-400 mesh column chromatography silica gel, and the eluent is: petroleum ether: ethyl acetate=100:0.5, v:v), the product can be obtained 2-Methoxybiphenyl, the yield was 82%.

[0060] The structural characterization data of the product are as follows:

[0061] 1 H NMR (400MHz, CDCl 3 )δ7.57–7.54(m,2H),7.45–7.41(m,2H),7.36–7.33(m,3H),7.08–7.00(m,2H),3.83(s,3H).MS(CI) Calcd for C 13 h 12 O:184; Found(M+H + ):185.

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Abstract

The invention discloses a synthesis method of biaryl compounds. The method comprises the following step: enabling iodoaromatic compounds to react with aromatic hydrocarbon compounds in the presence ofa urea derivative catalyst and additives so as to obtain the biaryl compounds. According to the synthesis method of the biaryl compounds, all the steps are carried out in one reactor, and a separation step is not needed during synthesis, so that the reaction belongs to a one-pot reaction, the reaction yield is increased, and the reaction product is easy to purify. The synthesis method provided bythe invention uses a series of urea derivatives as the catalyst, and a single electron transfer process occurs between the catalyst and reactants so as to form free radicals, so that a C-C bond is further catalyzed to be formed, and biaryl is produced. Compared with the traditional transition metal catalysis method, the catalyst is cheap and easy to obtain, has good selectivity, high yield and strong applicability, and is easy to treat after the reaction is finished, so that the cost is lowered and the synthesis rate is increased.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing biaryl compounds. Background technique [0002] Biaryl compounds are one of the important structures for building many natural organic compounds. It is widely used in the fields of organic functional materials (such as liquid crystal compounds, fluorescent compounds, etc.), medicine, pesticides, and organic synthesis intermediates. For example: biaryl compounds can be used as specific medicines for some stubborn diseases and as food additives in the food industry, so biaryl compounds have good development prospects. [0003] There are many reports on the synthesis of biaryls at home and abroad, and each has its own advantages. It mainly contains the following synthetic methods: (1) Fritz Ullmann et al. reported in 1901 that using halogenated aromatics as raw materials, using excessive new copper powder as a catalyst, and then directly heated ...

Claims

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Application Information

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IPC IPC(8): C07C1/26C07C15/14C07C17/269C07C25/18C07C41/30C07C43/205C07C253/30C07C255/50C07D333/08C07D213/16C07D213/127B01J31/02
CPCB01J31/0249B01J2231/4205C07C1/26C07C17/269C07C41/30C07C253/30C07C2531/02C07D213/127C07D213/16C07D333/08C07C15/14C07C25/18C07C43/205C07C255/50
Inventor 赵怀庆许缃雯吴畏张蔚张云仙
Owner UNIV OF JINAN
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