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Preparation method of acetyl thiophene

A technology of acetylthiophene and thiophene, which is applied in the field of preparation of acetylthiophene, can solve the problems that the reaction medium is not easy to volatilize, the organic solvent is easy to volatilize, and it is difficult to industrialize production, and achieve good solubility, easy industrial production, and non-volatile effects

Inactive Publication Date: 2007-01-17
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to solve the deficiencies in the prior art that the palladium catalyst in the preparation of acetylthiophene is expensive, difficult to carry out industrialized production, and the use of organic solvents is volatile and poor in solubility, the invention provides a method using nickel metal as a catalyst and ionic liquid as a reaction medium, A method for synthesizing acetylthiophene with low cost, easy industrial production, non-volatile reaction medium, and good solubility to both organic and inorganic substances

Method used

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Examples

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Effect test

Embodiment 1

[0031] Example 1: Preparation of 2-acetylthiophene from 2-bromothiophene

[0032] 163 mg (1 mmol) of 2-bromothiophene, 26 mg (0.1 mmol) of nickel acetate, 49 mg (0.12 mmol) of 1,3-bis(diphenylsulfone)propane, 500 mg of n-butyl vinyl ether mg (5 mmol), 20 mg (0.2 mmol) of triethylamine, 2 ml of 1-butyl-3-methylimidazolium tetrafluoroborate, placed in a 20 ml flask, stirred and heated, and reacted at 120°C 30 hours. After the reaction was over, it was cooled. After the product was extracted with toluene, the ionic liquid was dissolved in water, and then extracted once with toluene. The toluene solutions were combined, dried, concentrated, and separated by column chromatography to obtain 113 mg of the product with a yield of 90%.

[0033] 1 H NMR (CDCl 3 )δ: 2.57(s, 3H), 7.14(m, 1H), 7.64(m, 1H), 7.71(m, 1H); 13 CNMR (CDCl 3 )δ: 27.32, 128.5, 132.9, 134.2, 145.0, 191.2.

[0034] MS (m / z): 126 (M + ).

Embodiment 2

[0035] Example 2: Preparation of 3-acetylthiophene from 3-bromothiophene

[0036] 163 mg (1 mmol) of 3-bromothiophene, 26 mg (0.1 mmol) of nickel acetate, 49 mg (0.12 mmol) of 1,3-bis(diphenylsulfone)propane, 500 mg of n-butyl vinyl ether mg (5 mmol), 20 mg (0.2 mmol) of triethylamine, 2 ml of 1-butyl-3-methylimidazolium tetrafluoroborate, placed in a 20 ml flask, stirred and heated, and reacted at 120°C 30 hours. After the reaction was over, it was cooled. After the product was extracted with toluene, the ionic liquid was dissolved in water, and then extracted once with toluene. The toluene solutions were combined, dried, concentrated, and separated by column chromatography to obtain 111 mg of the product with a yield of 88%.

[0037] 1 H NMR (CDCl 3 )δ: 2.51(s, 3H), 7.31(m, 1H), 7.54(m, 1H), 8.04(m, 1H); 13 CNMR (CDCl 3 )δ: 27.40, 126.8, 127.3, 132.5, 143.1, 192.7.

[0038] MS (m / z): 126 (M + ).

Embodiment 3

[0039] Example 3: Preparation of 3-acetylthiophene from 3-chlorothiophene

[0040] 119 mg (1 mmol) of 3-chloropyridine, 26 mg (0.1 mmol) of nickel acetate, 49 mg (0.12 mmol) of 1,3-bis(diphenylsulfone) propane, 500 mg of n-butyl vinyl ether mg (5 mmol), 20 mg (0.2 mmol) of triethylamine, 2 ml of 1-butyl-3-methylimidazolium tetrafluoroborate, placed in a 20 ml flask, stirred and heated, and reacted at 120°C 30 hours. After the reaction was over, it was cooled. After the product was extracted with toluene, the ionic liquid was dissolved in water, and then extracted once with toluene. The toluene solutions were combined, dried, concentrated, and separated by column chromatography to obtain 101 mg of the product with a yield of 80%.

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Abstract

A process for preparing acetylthiophene incldues such steps as reaction of halothiophene on vinylether in ionic liquid under existance of Ni catalyst, ligand and organic amine while stirring, separating and purifying.

Description

(1) Technical field [0001] The invention relates to a preparation method of acetylthiophene. (2) Background technology [0002] Acetylthiophene is an important chemical raw material and an important intermediate of many drugs. It is generally easier to introduce an acetyl group on the ring of the thiophene heterocyclic compound at the 2-position of the ring, mainly using carboxyl derivatives to directly carry out electrophilic acylation reaction under the catalysis of Lewis acid, and through some carbocation active The intermediate is an indirect reaction in which aromatics undergo electrophilic substitution, and then decompose and convert to acyl groups. However, it is more difficult to acetylate the 3-position of the ring by the above method. [0003] The Heck reaction is an important method for the synthesis of alkenyl-substituted arenes from halogenated arenes under metal palladium catalysis. Due to the high price of metal palladium, it is difficult to carry out indus...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/24
Inventor 裴文孙莉肖建良
Owner ZHEJIANG UNIV OF TECH
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