A kind of synthetic method of 2-phenylthiobenzoic acid

A kind of technology of phenylthiobenzoic acid and synthetic method, applied in the direction of thioether preparation, organic chemistry, etc., can solve the problems of expensive phosphorus ligand, expensive palladium catalyst, limit the application of palladium catalytic system, etc., and achieve easy industrial production and low toxicity Small, easy to industrialize the effect of production

Inactive Publication Date: 2018-02-06
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the palladium catalyst itself is expensive, and the phosphorus ligands commonly used in the catalytic system are also relatively expensive. These two reasons greatly limit the application of the palladium catalytic system.

Method used

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  • A kind of synthetic method of 2-phenylthiobenzoic acid
  • A kind of synthetic method of 2-phenylthiobenzoic acid
  • A kind of synthetic method of 2-phenylthiobenzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1 (2: 1, sodium hydroxide, copper sulfate, DL-proline)

[0025] Add 0.35mmol (0.0539g) of thiosalicylic acid and 0.70mmol (0.0853g) of phenylboronic acid into the reaction tube, add 0.25mL of sodium hydroxide solution (10%), 0.05mL of anhydrous ethylenediamine, and then add 0.025mL of copper sulfate mmol (0.0040g) and DL-proline 0.025mmol (0.0029g) were used as catalysts, heated to 130°C for reaction, TLC tracking detection, the reaction was complete after 24 hours, TLC tracking determined that the reactants disappeared, and then naturally cooled to room temperature, the mother liquor Extracted with 170ml of ethyl acetate, took the organic layer and dried it with anhydrous magnesium sulfate, and spun to dry the solvent to obtain a solid. First pass through the column with petroleum ether with a boiling range of 60-90°C, load the crude product, then pass through the column with petroleum ether with a boiling range of 60-90°C, and then use a boiling range of 60...

Embodiment 2

[0026] Embodiment 2 (2: 1, sodium hydroxide, copper sulfate, DL-alanine)

[0027] Add 0.35mmol (0.0539g) of thiosalicylic acid and 0.70mmol (0.0853g) of phenylboronic acid into the reaction tube, add 0.25mL of sodium hydroxide solution (10%), 0.05mL of anhydrous ethylenediamine, and then add 0.025mmol of copper sulfate (0.0040g) and DL-alanine 0.025mmol (0.0022g) as a catalyst, heated to 130 ° C for reaction, TLC tracking detection, the reaction was complete in 24 hours, TLC tracking determined that the reactant thiosalicylic acid disappeared, and then cooled naturally After reaching room temperature, the mother liquor was extracted with 170 ml of ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated to dryness to obtain a solid. First pass through the column with petroleum ether with a boiling range of 60-90°C, load the crude product, then pass through the column with petroleum ether with a boiling range of 60-90°C, and th...

Embodiment 3

[0028] Embodiment 3 (2: 1, sodium hydroxide, copper sulfate, 8-hydroxyquinoline)

[0029]Add 0.35mmol (0.0539g) of thiosalicylic acid and 0.70mmol (0.0853g) of phenylboronic acid into the reaction tube, add 0.25mL of sodium hydroxide solution (10%), 0.05mL of anhydrous ethylenediamine, and then add 0.025mmol of copper sulfate (0.0040g) and 0.025mmol (0.0036g) of 8-hydroxyquinoline as a catalyst, heated to 130 ° C for reaction, TLC tracking detection, the reaction was complete in 24 hours, TLC tracking determined that the reactant thiosalicylic acid disappeared, and then cooled naturally After reaching room temperature, the mother liquor was extracted with 170 ml of ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated to dryness to obtain a solid. First pass through the column with petroleum ether with a boiling range of 60-90°C, load the crude product, then pass through the column with petroleum ether with a boiling range ...

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Abstract

The invention discloses a synthetic method of 2-thiophenylbenzoic acid. The synthetic method is characterized by including the steps of: 1) dissolving raw materials, comprising phenylboric acid represented as the formula I and thiosalicylic acid represented as the formula II, in an alkaline solution and adding anhydrous ethylenediamine; 2) in the presence of a metal salt catalyst and a ligand, carrying out a heating reaction at higher than 100 DEG C for more than 16 h with TLC tracing detection, and when then reactant, thiosalicylic acid, disappears, the reaction is determined to be finished; 3) naturally cooling the mixture to room temperature to obtain a mother liquid, extracting the mother liquid with ethyl acetate, drying an organic layer with anhydrous magnesium sulfate, and performing reduced-pressure rotary evaporation to remove the solvent and obtain a solid; and 4) purifying the solid crude product through a silica gel column, collecting an eluent, and performing rotary evaporation to dry the eluent to obtain the 2-thiophenylbenzoic acid represented as the formula III. The method is simple in reaction conditions and high in yield, is easy to enlarge in large scale, and is environment-friendly and low-pollution.

Description

technical field [0001] The invention relates to a synthesis method of compounds containing aryl sulfide fragment molecules, in particular to a synthesis method of 2-phenylthiotoluic acid. Background technique [0002] Molecules containing aryl sulfide moieties (that is, organic compounds containing C-S bonds in molecules) are a very important class of compounds. They are not only important structural units of many natural products and biologically active molecules, but also exist in many drug structures, or An important component of many functional polymer materials. Therefore, it is particularly important to construct new C-S bonds from some sulfur-containing compounds with simple structures for the application of such compounds. [0003] In 1901, Ullmann (Ullmann) first reported the synthesis of biaryl hydrocarbons, and the cross-coupling of bonds such as C-N, C-O, and C-S has been reported one after another. This type of coupling reaction is usually collectively referred...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/62C07C319/14
Inventor 李新华王彩霞肖洪平赵亚娟
Owner WENZHOU UNIV
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