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Synthesis of 3, 5-dibromo-4-iodopyridine

A kind of technology of fluoropyridine and aminopyridine is applied in the synthesis field of halopyridine, and achieves the effect of good economic benefit and social benefit

Inactive Publication Date: 2013-01-30
XIHUA UNIV
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  • Summary
  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Although the halopyridine 3,5-dibromo-4-fluoropyridine containing fluorine and bromine is equally important in the fields of medicine, pesticides, functional materials, etc., so far there is no published literature report on 3,5-dibromo-4-fluoropyridine Efficient synthetic method of -fluoropyridine

Method used

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  • Synthesis of 3, 5-dibromo-4-iodopyridine
  • Synthesis of 3, 5-dibromo-4-iodopyridine

Examples

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Embodiment 1

[0021] Synthesis of 3,5-dibromo-4-aminopyridine (bromination reaction): Add 400ml of solvent carbon tetrachloride, 47.05g (0.5mol) of 4-aminopyridine, azobisisobutyl Nitrile etc. (AIBN) 0.41g, add N-bromosuccinimide (NBS) 195.78g (1.1mol) in batches at 20°C, then raise the temperature to 50°C for 4 hours, TLC board monitors the raw material 4-amino Pyridine and the intermediate 3-bromo-4-aminopyridine are converted into the target product 3,5-dibromo-4-aminopyridine, and the reaction is stopped. Post-reaction treatment: the reaction solution was stirred and cooled to room temperature, filtered, the filter cake was fully washed with carbon tetrachloride several times, the filtrate was washed once with aqueous sodium bicarbonate solution, once with saturated saline, and the solvent carbon tetrachloride was removed by rotary evaporation , the obtained 3,5-dibromo-4-aminopyridine crude product was 120.60 g, and the crude product was directly used in the next reaction.

[0022] Sy...

Embodiment 2

[0024] The bromination reagent was 314.51 g (1.1 mol) of 1,3-dibromo-5,5-dimethylhydantoin, and other operations were the same as in Example 1.

[0025] The operation was carried out according to Example 1, and 97.0 g of pure white 3,5-dibromo-4-fluoropyridine was obtained, with a content of 98.6% and a yield of 76.1%.

Embodiment 3

[0027] Described bromination reaction initiator is 0.61g of benzoyl peroxide, and other are the same as operation embodiment 1.

[0028] The operation was carried out according to Example 1, and 102.2 g of pure white 3,5-dibromo-4-fluoropyridine was obtained, with a content of 99.0% and a yield of 80.2%.

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Abstract

The invention discloses a synthesis method of halogenated pyridine-3, 5-dibromo-4-iodopyridine, wherein 4-aminopyridine is taken as an initial material and is subjected to bromination reaction to produce a 3, 5-dibromo-4-aminopyridine midbody, and the midbody is subjected to diazo-reaction to obtain the 3, 5-dibromo-4-iodopyridine. The process route has the characteristics of being good in selectivity, and simple in operation, the yield is high and the initial material acquisition is easy.

Description

technical field [0001] The present invention relates to a synthetic method of halogenated pyridine, especially a synthetic method of 3,5-dibromo-4-fluoropyridine. Background technique [0002] Halopyridines are important fine chemical intermediates and are widely used in the fields of medicine and pesticides. Due to the particularity of the fluorine atom, the fluorine-containing halogenated pyridines are widely used in the fields of pesticides, medicines, and functional materials. German patent (DE2241665,1975) reported the synthesis of herbicides using fluorine-bromine-containing halogenated pyridine 2,4-difluoro-3,5,6-tribromopyridine as a key intermediate; world patent (WO2003 / 99816A1) reported The acceptor drug of GABA is synthesized by using the halogenated pyridine 2,3,5,6-tetrafluoro-4-bromopyridine containing fluorine and bromine as the key intermediate; US Patent (US5205962A1, 1993) reported the use Pyridine 2,6-difluoro-3-bromopyridine is used as the key interm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61
Inventor 杨维清倪小惠胡伟发马梦林张园园
Owner XIHUA UNIV
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