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Synthetic method of biphenyl compounds

A synthesis method and compound technology, which is applied in the field of synthesis of biphenyl compounds, can solve problems such as unreported and harsh reaction conditions, and achieve the effects of simple operation, high reaction efficiency, and a wide range of substrates

Inactive Publication Date: 2014-02-05
TONGJI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction conditions are harsh and the yield needs to be improved (J. Chem. Soc ., Perkin Trans. 1, 2001, 3042–3045)
[0006] So far, the method of Suzuki coupling by phenylhydrazine or benzenesulfonylhydrazine and phenylboronic acid has not been reported, the present invention provides a highly efficient The method for synthesizing biphenyl compounds with phenylhydrazine or benzenesulfonylhydrazine

Method used

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  • Synthetic method of biphenyl compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of p-methoxybiphenyl

[0023]

[0024] Phenylhydrazine ( 1 ) (0.03 mmol), p-methoxyphenylboronic acid ( 2 ) (0.06 mmol), tetrakistriphenylphosphopalladium (0.0009mmol), sodium carbonate (0.06mmol) and toluene (1 ml) mixed solvent, stirred at 40 ℃ for 2 hours. After the reaction was completed, filtered, the organic phase was combined, Concentrated crude product. The crude product was subjected to column separation with ethyl acetate / petroleum ether=1:10 as the eluent to obtain the desired product. The yield is 91%.

[0025] 1 H NMR (400 MHz, CDCl 3 ) δ 7.54 (t, J = 8.2 Hz,4H), 7.42 (t, J = 7.6 Hz, 2H), 7.30 (t, J = 7.4 Hz, 1H), 6.98 (d, J = 8.7 Hz, 2H), 3.85 (s, 3H).

Embodiment 2

[0026] Embodiment 2: the synthesis of 3-methoxybiphenyl

[0027]

[0028] Phenylhydrazine ( 1 ) (0.03 mmol), 3-methoxyphenylboronic acid ( 2 ) (0.06 mmol), tetrakistriphenylphosphopalladium (0.0009mmol), sodium carbonate (0.06mmol) and toluene (1 ml) mixed solvent, stirred at 40 ℃ for 2 hours. After the reaction was completed, filtered, the organic phase was combined, Concentrated crude product. The crude product was subjected to column separation with ethyl acetate / petroleum ether=1:10 as the eluent to obtain the desired product. The yield is 92%.

[0029] 1 H NMR (400 MHz, CDCl3) δ 7.59 (d, J = 7.2 Hz, 2H), 7.44 (t, J = 7.5 Hz, 2H), 7.39 – 7.32 (m, 2H), 7.18 (d, J= 7.8 Hz, 1H), 7.13 (d, J = 1.9 Hz, 1H), 6.90 (dd, J = 8.2, 1.9 Hz, 1H), 3.87 (s, 3H).

Embodiment 3

[0030] Embodiment 3: the synthesis of 2-methoxybiphenyl

[0031]

[0032] Phenylhydrazine ( 1 ) (0.03 mmol), 2-methoxyphenylboronic acid ( 2 ) (0.06 mmol), tetrakistriphenylphosphopalladium (0.0009mmol), sodium carbonate (0.06mmol) and toluene (1 ml) mixed solvent, stirred at 40 ℃ for 2 hours. After the reaction was completed, filtered, the organic phase was combined, Concentrated crude product. The crude product was subjected to column separation with ethyl acetate / petroleum ether=1:10 as the eluent to obtain the desired product. Yield 86%.

[0033] 1 H NMR (400 MHz, CDCl3) δ 7.53 (d, J = 7.2 Hz, 2H), 7.41 (t, J = 7.5 Hz, 2H), 7.33 (ddd, J = 6.8, 4.3, 2.4 Hz, 3H), 7.08 – 6.95 (m, 2H), 3.82 (s, 3H).

[0034]

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Abstract

The invention relates to a synthetic method of biphenyl compounds. Based on novel coupling reaction of phenylhydrazine or benzenesulfonyl hydrazide, the phenylhydrazine or benzenesulfonyl hydrazide is used as a substrate, and coupled after being acted by transition metal in a catalytic manner, so that the biphenyl compounds can be conveniently and effectively combined. Compared with the existing method, the synthetic method disclosed by the invention is extensive in applicable substrate range, mild in reaction condition, simple and convenient to operate and high in reaction efficiency, and is a method with important application value. The method disclosed by the invention is further used for synthesizing biphenyl compounds containing halogens. The invention provides a simple, novel and efficient method.

Description

technical field [0001] The invention belongs to the technical field of organic and pharmaceutical synthesis, and in particular relates to a synthesis method of biphenyl compounds. Background technique [0002] Suzuki reaction, also known as Suzuki coupling reaction, Suzuki-Miyaura reaction (Suzuki-Miyaura reaction) (N.Miyaura and A.Suzuki, Chem. Rev., 1995, 95, 2457), is a relatively new organic couple Cross-coupling of aryl or alkenyl boronic acid or boronic acid ester with chlorine, bromine, iodoarenes or alkenes under the catalysis of zero-valent palladium complex. This reaction was first reported by Akira Suzuki in 1979. It is widely used in organic synthesis and has strong substrate adaptability and functional group tolerance. Suzuki coupling plays an important role in the synthesis of biphenyl compounds and drug synthesis. Due to the wide application value of this kind of method, it has attracted extensive attention in the fields of organic synthesis and drug synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/04C07C43/205C07C41/30C07C205/06C07C201/12
Inventor 匡春香李亚辉
Owner TONGJI UNIV
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