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Preparation method of 2-halogen-6-alkylthio toluene

A technology of alkylthiotoluene and dimethyl sulfoxide, applied in the field of compound preparation, can solve the problems of high cost, low yield, complicated operation of 2-halogenated-6-alkylthiotoluene, etc. The effect of high yield and simple steps

Active Publication Date: 2016-10-12
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to overcome the defects of complex operation, high cost and low yield in the preparation of 2-halogenated-6-alkylthiotoluene in the prior art, and provide a preparation method of 2-halogenated-6-alkylthiotoluene

Method used

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  • Preparation method of 2-halogen-6-alkylthio toluene

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preparation example Construction

[0014] The present invention provides a kind of preparation method of the 2-halo-6-alkylthiotoluene shown in formula (1), it is characterized in that, this method comprises: the aqueous solution of the compound shown in formula (3) and as The dimethyl sulfoxide of the solvent is mixed, the obtained mixture is dehydrated, and the material obtained after dehydration is contacted with the compound shown in formula (2);

[0015]

[0016] In formula (2), two R 1 Each is F, Cl or Br; preferably, two R 1 Each is Cl or Br; more preferably, two R 1 Both are Cl.

[0017] In formula (3), R 2 for C 1 -C 6 straight-chain or branched-chain alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, sec-pentyl, 1-ethylpropyl, 2-methylbutyl, tert-amyl, 1,2-dimethylpropyl, isopentyl, neopentyl, n-hexyl, sec-hexyl, tert-hexyl, isohexyl or neohexyl ; preferably, R 2 for C 1 -C 3 Straight-chain alkyl groups, such as methyl, ethyl, n-propyl; ...

Embodiment 1

[0036] This example is used to illustrate the preparation method of 2-chloro-6-methylthiotoluene.

[0037] Add 600g of dimethyl sulfoxide and 633g (1.81mol) of 20% sodium methyl mercaptide aqueous solution into a 2000mL four-necked reaction flask, and carry out water pump negative pressure distillation at 90°C and a vacuum of 2000Pa until there is a small amount of Methyl sulfoxide was distilled off, then 300g (1.81mol) of 2,6-dichlorotoluene was added into a 2000mL four-neck reaction flask, and reacted at 100°C for 3h. After the reaction, the temperature was lowered to 30°C, and 0.18 mol of methyl chloride was passed into the reaction system, and after stirring for 0.5 hours, suction filtration was performed, and the solid obtained by suction filtration was rinsed twice with dimethyl sulfoxide, and the filtrates were combined and carried out. Negative pressure rectification gave 220.6 g (1.27 mol) of 2-chloro-6-methylthiotoluene with a yield of 92.5%.

Embodiment 2

[0039] This example is used to illustrate the preparation method of 2-chloro-6-methylthiotoluene.

[0040]Add 1800g of dimethyl sulfoxide and 1269g (2.72mol) of 15% sodium methyl mercaptide aqueous solution into a 2000mL four-necked reaction flask, and carry out water pump negative pressure distillation at 60°C and a vacuum of 500Pa until there is a small amount of Methyl sulfoxide was distilled off, then 300g (1.81mol) of 2,6-dichlorotoluene was added into a 2000mL four-neck reaction flask, and reacted at 80°C for 1h. After the reaction, the temperature was lowered to 20°C, and 0.091 mol of methyl chloride was introduced into the reaction system. After stirring for 0.5 hours, suction filtration was carried out, and the solid obtained by suction filtration was rinsed twice with dimethyl sulfoxide, and the filtrates were combined and carried out. Negative pressure rectification gave 184.9 g (1.05 mol) of 2-chloro-6-methylthiotoluene with a yield of 93.7%.

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Abstract

The invention relates to the compound preparation field, and discloses a preparation method of 2-halogen-6-alkylthio toluene, wherein the method comprises the steps: mixing a sodium alkyl sulfhydryl aqueous solution and dimethyl sulfoxide as a solvent, dehydrating the obtained mixture, and carrying out a contact reaction of the material obtained after dehydration with a substrate compound. The method has the advantages of simple operation, low cost and high yield, and is suitable for large-scale industrialized production.

Description

technical field [0001] The invention relates to the field of compound preparation, in particular to a preparation method of 2-halo-6-alkylthiotoluene. Background technique [0002] The invention relates to the field of compound preparation. 2-halo-6-alkylthiotoluene is an intermediate for preparing the pesticide herbicide tembotrione. [0003] WO2000021924 and Tetrohedron Letters (1980, 21 volumes, 3099-3100 pages) disclose a kind of preparation method of benzoylcyclohexanedione, and this method reacts with anhydrous solid sodium methyl mercaptide and hexaphosphine to prepare 2 -Chloro-6-methylthiotoluene. The yield of this method is high, and reaction is fast, but, because hexaphosphamide price is high, anhydrous solid sodium methyl mercaptide is difficult to obtain, and price is high, causes this method cost high. [0004] WO2008066033 discloses a method for preparing alkylthio-substituted benzene derivatives. The method uses 1,3-dimethyl-2-imidazolidinone as a solvent, ...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C323/09
CPCC07C319/14C07C323/09
Inventor 吴国林霍世勇路凤奇金辰张艳芳
Owner NUTRICHEM LAB CO LTD
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