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Method for preparing 3-bromo-4-methanesulfonylpyridine

A technology of methanesulfonylpyridine and dibromopyridine, which is applied in the field of preparing 3-bromo-4-methanesulfonylpyridine, can solve the problem of low yield of 3-bromo-4-methanesulfonylpyridine, cumbersome operation, inconvenience, etc. question

Active Publication Date: 2019-11-05
CHANGZHOU UNIV
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Problems solved by technology

The defect that this method exists: the first, the yield of target product 3-bromo-4-methanesulfonylpyridine is relatively low, and the yield of bibliography to second-step reaction only has 41%; The 2nd, this reaction passes two-step reaction To build the target product, the operation is cumbersome and not easy

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  • Method for preparing 3-bromo-4-methanesulfonylpyridine

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specific Embodiment

[0014] Add dimethylsulfoxide (4.0mL), 3,4-dibromopyridine (5mmol, 1.185g), sodium methylsulfinate (6mmol, 0.613g) and ketone iodide successively into a 50mL pressure tube (0.5mmol, 0.095g), L-proline (1.0mmol, 0.115g), the reaction temperature was controlled at 100 degrees Celsius, and the reaction was vigorously stirred for 24 hours. After the reaction was completed, it was cooled to room temperature, and the reaction liquid was concentrated and separated by column chromatography in sequence to obtain the target product 3-bromo-4-methanesulfonylpyridine (1.06 g, 90%).

[0015] The equations involved in the reaction are as follows:

[0016]

[0017] The NMR data and mass spectrum data of the target product 3-bromo-4-methanesulfonylpyridine are as follows:

[0018] 1 H NMR (300MHz, CDCl 3 )δ8.90(s,1H),8.75(d,J=5.0Hz,1H),7.95(d,J=4.8Hz,1H),3.23(s,3H).

[0019] 13 C NMR (75MHz, CDCl 3 )δ154.59, 149.92, 147.00, 123.58, 117.65, 42.03.

[0020] Ms(EI):m / z=234.95,236.95[M ...

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Abstract

The invention relates to the technical field of fine chemical engineering, and discloses a method for preparing 3-bromo-4-methanesulfonylpyridine. The method is characterized in that 3,4-dibromopyridine and sodium methylsulfinate which are used as raw materials are reacted in dimethyl sulfoxide at 100 DEG C for 24 h with cuprous iodideas a catalyst and L-proline as an additive to obtain the targetproduct 3-bromo-4-methanesulfonylpyridine. The method is simple to operate, uses the 3,4-dibromopyridine and sodium methylsulfinate as the reaction raw materials to efficiently synthesize the targetproduct in one step, has potential industrial values, and is worthy of promotion and application.

Description

technical field [0001] The invention belongs to the field of fine chemicals and relates to a method for preparing 3-bromo-4-methanesulfonylpyridine. Background technique [0002] 3-Bromo-4-methylsulfonylpyridine is an important class of organic compounds, which widely exist in various natural products and medicines, and these compounds are also important intermediates in organic synthesis. Therefore, how to directly and efficiently synthesize 3-bromo-4-methylsulfonylpyridine has attracted great attention of chemists. [0003] At present, the reported synthesis method of 3-bromo-4-methylsulfonylpyridine (PCT Int.Appl.2016180537) is mainly synthesized in two steps: first, the corresponding 4-methylthio-3-bromopyridine; secondly, oxidize 4-methylthio-3-bromopyridine with m-chloroperoxybenzoic acid to generate corresponding 3-bromo-4-methylsulfonylpyridine. The defect that this method exists: the first, the yield of target product 3-bromo-4-methanesulfonylpyridine is relativel...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/71
CPCC07D213/71
Inventor 杨科宋梦杰马志艳范鑫鑫李正义
Owner CHANGZHOU UNIV