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A method for preparing 3-bromo-4-methanesulfonylpyridine

A technology of methanesulfonylpyridine and dibromopyridine, which is applied in the field of preparation of 3-bromo-4-methanesulfonylpyridine, can solve the problem of low yield of 3-bromo-4-methanesulfonylpyridine, cumbersome operation, not simple, etc. question

Active Publication Date: 2022-06-28
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

Method used

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  • A method for preparing 3-bromo-4-methanesulfonylpyridine

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specific Embodiment

[0013] Dimethyl sulfoxide (4.0 mL), 3,4-dibromopyridine (5 mmol, 1.185 g), sodium methanesulfinate (6 mmol, 0.613 g), and iodide iodide were successively added to a 50 mL pressure-resistant tube. (0.5 mmol, 0.095 g), L-proline (1.0 mmol, 0.115 g), the inverse 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 solution was concentrated and separated by column chromatography in sequence to obtain the target product 3-bromo-4-methanesulfonylpyridine (1.06 g, 90%).

[0014] The equation involved in the reaction is as follows:

[0015]

[0016] The NMR data and mass spectrometry data of the target product 3-bromo-4-methanesulfonylpyridine are as follows:

[0017] 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).

[0018] 13 C NMR (75MHz, CDCl 3 )δ154.59,149.92,147.00,123.58,117.65,42.03.

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Abstract

The invention relates to the technical field of fine chemicals, and discloses a method for preparing 3-bromo-4-methylsulfonylpyridine. Concrete steps: take 3,4-dibromopyridine and sodium methylsulfinate as raw materials, ketone iodide as a catalyst, and L-proline as an additive, and react in dimethyl sulfoxide at 100 degrees Celsius for 24 hours, namely The target product 3-bromo-4-methylsulfonylpyridine can be obtained. This method is easy to operate, uses 3,4-dibromopyridine and sodium methanesulfinate as reaction raw materials, and can efficiently synthesize the target product in one step. It has potential industrial value and is worthy of popularization 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-methanesulfonylpyridine is an important class of organic compounds, which are widely present in various natural products and medicines, and are also important intermediates in organic synthesis. Therefore, how to directly and efficiently synthesize 3-bromo-4-methanesulfonylpyridine has attracted great attention of chemists. [0003] At present, the reported synthetic method of 3-bromo-4-methanesulfonylpyridine (PCT Int.Appl.2016180537) is mainly synthesized through two steps: first, the corresponding 3,4-dibromopyridine is reacted with sodium methanethiolate to generate the corresponding 4-methylthio-3-bromopyridine; secondly, 4-methylthio-3-bromopyridine is oxidized with m-chloroperoxybenzoic acid to generate the corresponding 3-bromo-4-methanesulfonylpyridine. The defects of this metho...

Claims

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Application Information

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Patent Type & Authority Patents(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
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