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A kind of reductive coupling method between p-toluenesulfonyl oxo compounds

A technology of toluenesulfonyl oxo compounds and compounds, which is applied in the field of synthesis of organic compounds, can solve problems such as not being suitable for mass production and expensive catalysts, and achieve the effects of low production cost, high productivity and few by-products

Active Publication Date: 2015-10-14
HUNAN FARIDA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Literature (Dyes and Pigments 96(2013) 756-762) reported the use of magnesium powder, Ni(dppf)Cl 2 Self-coupling of 2-bromothiophene, the catalyst used is expensive and not suitable for mass production

Method used

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  • A kind of reductive coupling method between p-toluenesulfonyl oxo compounds
  • A kind of reductive coupling method between p-toluenesulfonyl oxo compounds
  • A kind of reductive coupling method between p-toluenesulfonyl oxo compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of 1,6-diphenyl-n-hexane

[0026]

[0027] Put a suitable magnetic stirrer, 2.5mg of cuprous iodide and 12mg of magnesium powder into a dry 10mL Schlenk tube, vacuumize the Schlenk tube with an oil pump for 2 minutes, and then flush argon into the tube, this operation repeat three times. Add 0.5mL THF (after anhydrous treatment), 1mol 3-p-toluenesulfonyloxypropylbenzene and 0.05mol 2-bromofuran to the Schlenk tube successively with a syringe, seal the reaction tube, Stir at room temperature for about 5 minutes, place the reaction tube in a previously heated 100°C oil bath, and stir for 24 hours. After the reaction, the reactant was cooled to room temperature and distilled under reduced pressure. The obtained crude product was separated and purified by chromatographic column and dried overnight in vacuum to obtain 108 mg of the target product 1,6-diphenyl-n-hexane with a yield of 91%.

Embodiment 2

[0028] Embodiment two: the preparation of 1-phenyl pentadecane

[0029]

[0030] Put a suitable magnetic stirrer, 2.5mg of cuprous iodide and 12mg of magnesium powder into a dry 10mL Schlenk tube, vacuumize the Schlenk tube with an oil pump for 2 minutes, and then flush argon into the tube, this operation repeat three times. Add 0.5mL THF (after anhydrous treatment), 0.8mol 3-p-toluenesulfonyloxypropylbenzene, 0.5mol 1-p-toluenesulfonate to the Schlenk tube in sequence with argon Acyloxydodecane and 0.05mol 2-bromofuran, seal the reaction tube, stir at room temperature for about 5 minutes, place the reaction tube in a pre-heated 10°C oil bath, and stir for 2 hours. After the reaction, the reactant was cooled to room temperature and distilled under reduced pressure. The obtained crude product was separated and purified by chromatographic column, and dried overnight in vacuum to obtain 104 mg of the target product 1-phenylpentadecane with a yield of 72%.

Embodiment 3

[0031] Embodiment three: the preparation of 1-phenyl-4-methyldecane

[0032]

[0033] Put a suitable magnetic stirrer, 2.5 mg of cuprous iodide and 12 mg of magnesium powder into a dry 10 mL Schlenk tube, vacuumize the Schlenk tube with an oil pump for 2 minutes, and then flush argon into the tube. repeat three times. Add 0.5mL THF (after anhydrous treatment), 0.8mol 3-p-toluenesulfonyloxypropylbenzene, 0.5mol 2-p-methylbenzenesulfonate to the Schlenk tube in sequence with argon Acyloxyoctane and 0.05mol 2-bromofuran, seal the reaction tube, stir at room temperature for about 5 minutes, place the reaction tube in a previously heated 25°C oil bath, and stir for 10 hours. After the reaction, the reactant was cooled to room temperature and distilled under reduced pressure. The obtained crude product was separated and purified by chromatographic column and dried overnight in vacuum to obtain 52 mg of the target product 1-phenyl-4-methyldecane with a yield of 45%.

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Abstract

The invention discloses a reductive coupling method of p-methyl benzenesulfonyl oxo-compounds. The method comprises the following steps: mixing two p-methyl benzenesulfonyl oxo-compounds in a non-polar solvent; adding 100-200 parts by weight of magnesium powder or metal magnesium fine particles, 0-10 parts by weight of a copper salt catalyst and 0-20 parts by weight of bromide to perform reaction for 2-24 hours under the water-free and oxygen-free conditions to obtain a corresponding reductive coupling product. The method disclosed by the invention replaces the conventional multi-step reaction; the coupling method is controllable, a coupling target product can be obtained in a low-temperature neutral process without ligands and alkali; a required Grignard reagent can be obtained in one-step reaction. The reductive coupling method disclosed by the invention is simple and convenient to operate, is stable, environmental friendly, wide in application, environmental friendly and non-toxic in production and less in byproduct, is easy to separate, and is low in production cost and high in production rate.

Description

technical field [0001] The invention relates to a synthesis method of organic compounds, in particular to a reductive coupling method between p-toluenesulfonyl oxo compounds. Background technique [0002] Reductive coupling reaction is also known as reductive coupling reaction and reductive coupling reaction. It is a process in which two organic chemical units undergo a coupling reaction to form an organic molecule by adding a reducing agent. It is an important type of reaction in organic chemistry. , have very good application in medicine, pesticide, material chemistry. The p-toluenesulfonyl oxo compound can be prepared from cheap and easy-to-obtain alcohol with simple process, environmental protection and high yield. [0003] Traditionally, the methods used to couple two electrophiles are mostly two or more steps, such as the reaction between bromo compounds, first one of the bromo compounds is made into the corresponding Grignard reagent, and then Reaction with another ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/00C07C1/32C07C15/12C07C15/107
Inventor 胥松单文伟李玉新彭敏
Owner HUNAN FARIDA TECH CO LTD