Preparation method for trifluoromethyl benzothiophene derivative and purification method for product of preparation method

A technology of thiophene derivatives and trifluoromethylbenzene, which is applied in the field of preparation of trifluoromethylbenzothiophene derivatives, can solve the problems of pollution in the preparation process, complicated process flow, high production cost, etc., and achieves a cheap synthetic system , simple process and low cost

Inactive Publication Date: 2016-04-20
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, benzothiophene derivatives are academic research hotspots. Through retrieval, Organic Chemical Impurities 1995, 15, 245-251 reported "Synthesis of 6-trifluoromethyl benzothiophene derivative

Method used

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  • Preparation method for trifluoromethyl benzothiophene derivative and purification method for product of preparation method
  • Preparation method for trifluoromethyl benzothiophene derivative and purification method for product of preparation method
  • Preparation method for trifluoromethyl benzothiophene derivative and purification method for product of preparation method

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preparation example Construction

[0023] The preparation method of the trifluoromethylbenzothiophene derivative of the present embodiment comprises the following steps: taking the acetylenic alcohol compound containing fluoromethyl building blocks or its derivatives as the substrate, adding disulfide to the substrate, and The mol ratio of substance and disulfide is 1:0.6; Then take nitromethane solution as solvent dissolution, and in iodine simple substance, the amount of iodine simple substance is 2.0 equivalent; And in iron catalyst FeCl 3 , Benzoyl peroxide nitrogen atmosphere, the preferred FeCl 3 The molar percentage of benzoyl peroxide is 20%, and the molar percentage of benzoyl peroxide is 10%; Through 120 ℃ heating reaction 24h, make crude product, its chemical reaction formula is as follows:

[0024]

[0025] Wherein, R in the general formula of the substrate is one of methyl, tert-butyl, fluorine, chlorine, bromine, benzene, and hydrogen; R' is one of methyl, fluorine, chlorine, and hydrogen.

[...

specific Embodiment 1

[0032] Specific embodiment one: 20.0 mg (0.1 mmol) 4,4,4-trifluoro-1-phenyl-2-butyn-1-alcohol, 13.1 mg (0.06 mmol) diphenyl disulfide, 3.1 mg ( 0.02mmol) FeCl 3 , 2.5 mg (0.01 mmol) of benzoyl peroxide, 50.8 mg (0.2 mmol) of iodine in the reaction test tube, and then 2 mL of CH 3 NO 2 , heated at 120°C for 24 hours under a nitrogen atmosphere, cooled after the reaction, filtered, and the filtrate was rotary evaporated to remove excess iodine and solvent, and the residue was chromatographed on a silica gel column, washed with a mixture of petroleum ether and ethyl acetate, and TLC Detect, combine the effluents containing the product, distill off the solvent with a rotary evaporator, and dry in vacuo to obtain 22.0 mg of 2-trifluoroacetyl-3-phenylbenzothiophene as a yellow liquid with a yield of 72%. 1 HNMR (500MHz, CDCl 3 )δ7.84(d,J=8.0Hz,1H),7.51-7.47(m,2H),7.43-7.40(m,3H),7.33-7.32(m,1H),7.29-7.27(m,2H) ; 13 CNMR (125MHz, CDCl 3 )δ175.6(q,J C-F =37.1Hz), 148.6, 141.9, ...

specific Embodiment 2

[0034] Specific example two: 21.4 mg (0.1 mmol) 4,4,4-trifluoro-1-(4-tolyl)-2-butyn-1-alcohol, 13.1 mg (0.06 mmol) diphenyl disulfide , 3.1 mg (0.02 mmol) FeCl 3 , 2.5 mg (0.01 mmol) of benzoyl peroxide, 50.8 mg (0.2 mmol) of iodine in the reaction test tube, and then 2 mL of CH 3 NO 2 , heated at 120°C for 24 hours under a nitrogen atmosphere, cooled after the reaction, filtered, and the filtrate was rotary evaporated to remove excess iodine and solvent. The residue was subjected to silica gel column chromatography, washed with petroleum ether, and detected by TLC. liquid, the solvent was distilled off by a rotary evaporator, and dried in vacuo to obtain 25.9 mg of 2-trifluoroacetyl-3-(4-methylphenyl)benzothiophene as a yellow liquid, with a yield of 81%. 1 HNMR (500MHz, CDCl 3 )δ7.91(d, J=8.0Hz, 1H), 7.61(d, J=8.5Hz, 1H), 7.56-7.53(m, 1H), 7.40-7.36(m, 1H), 7.31-7.25(m ,4H),2.45(s,3H); 13 CNMR (125MHz, CDCl 3 )δ175.7(q,J C-F =36.9Hz), 148.8, 141.9, 139.7, 138.7, 130.8...

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Abstract

The invention discloses a preparation method for a trifluoromethyl benzothiophene derivative and a purification method for a product of the preparation method. The preparation method comprises the steps that an alkynol compound containing methyl fluoride building blocks or a derivative of the alkynol compound is taken as a substrate, disulfide is added into the substrate, and a crude product is prepared through a heating reaction under the nitrogen atmosphere of an elementary substance iodine, benzoyl peroxide and an iron catalyst by taking a nitromethane solution as solvent. The crude product is purified through the steps that filtering, iodine removing and solvent removing are performed on the crude product to obtain residua; chromatography is performed on the residua by adopting a silicagel column, elution is performed through eluent, and effluent is collected; the effluent containing the product is merged; concentrating and solvent removing are performed on the merged effluent, and vacuum drying is performed to obtain the target product. The preparation method and the purification method have the advantages of being simple in technological process, low in cost and high in yield.

Description

technical field [0001] The invention belongs to the field of organic compounds, in particular to a preparation method of trifluoromethyl-benzothiophene derivatives. Background technique [0002] Benzothiophene (BT) and its derivatives are important components of heterocyclic compounds. It is generally aromatic and has high stability. It is a kind of organic sulfur that is difficult to remove, and occupies a pivotal position in the research of petroleum desulfurization. At the same time, they have various reactivity, are important organic synthesis intermediates, and have important applications in the fields of pesticides, medicines, and dyes. [0003] At present, benzothiophene derivatives are academic research hotspots. Through retrieval, Organic Chemical Impurities 1995, 15, 245-251 reported "Synthesis of 6-trifluoromethyl benzothiophene derivatives", but the process has the following disadvantages: process flow Complexity, high raw material price, high production cost, ...

Claims

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Application Information

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IPC IPC(8): C07D333/56
CPCC07D333/56
Inventor 张兴国林炎锋张小红胡伯伦邓辰亮
Owner WENZHOU UNIVERSITY
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