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Preparation method of 3-trifluoromethyl phthalide

A technology of trifluoromethylphthalide and trifluoromethyltrimethylsilane is applied in the field of preparation of 3-trifluoromethylphthalide, can solve the problems of complicated operation, low reaction yield and the like, and achieves high reaction activity , the reaction operation is simple, the effect of low environmental damage

Inactive Publication Date: 2017-05-17
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Wherein, the bromotrifluoromethane that method (1) utilizes is a kind of poisonous gas, and the reaction needs specialized equipment, and reaction yield is lower; Method (2) needs the high temperature of 170 ℃; And method (3) and (4) The reaction needs to be strictly controlled under anhydrous and oxygen-free conditions, and the operation is complicated

Method used

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  • Preparation method of 3-trifluoromethyl phthalide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] At room temperature, methyl 2-formylbenzoate (1mmol), TMSCF 3 (1.2mmol) and potassium carbonate (1.0mmol) were miscible in 2mL DMF, and the mixture was stirred and reacted for 8h. After the reaction, water and ethyl acetate were added, and the organic phase was obtained by extraction, dried, and the organic solvent was removed by distillation under reduced pressure. The product 3-trifluoromethylphthalide was obtained by column chromatography with a yield of 87%.

Embodiment 2

[0016] Reaction steps are identical with embodiment 1, difference is:

[0017] The amount of potassium carbonate used was 0.75 mmol, and the yield of 3-trifluoromethylphthalide was 84%.

Embodiment 3

[0019] Reaction steps are identical with embodiment 1, difference is:

[0020] The amount of potassium carbonate used was 0.5 mmol, and the yield of 3-trifluoromethylphthalide was 83%.

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Abstract

The invention discloses a preparation method of 3-trifluoromethyl phthalide. The preparation method comprises steps as follows: after 2-formyl benzoate, trifluoromethyl trimethylsilane and potassium carbonate are proportionally mixed, an organic solvent is added, a mixture is stirred and reacts, a product is extracted with ethyl acetate and water after reaction, an organic phase is obtained through separation and dried, the solvent is removed through reduced-pressure distillation, and a product, namely, 3-trifluoromethyl phthalide is obtained through column chromatography. According to the preparation method of 3-trifluoromethyl phthalide, 2-formyl benzoate which is cheap and available is taken as a raw material, reactivity is high, reaction conditions are mild, and transition metal salt is not required to be added as a catalyst, so that environment hazards are reduced; with the adoption of one-pot two-step method for reaction, the product yield is high, few byproducts are produced, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 3-trifluoromethylphthalide. Background technique [0002] Due to the unique properties of fluorine atoms and fluorine-containing groups, such as trifluoromethyl, sulfur trifluoromethyl, etc., such as strong electronegativity, stability of carbon-fluorine bonds, lipophilicity and hydrophobicity, etc., in The introduction of fluorine atoms or fluorine-containing groups into the drug can change the acidity and alkalinity of the drug; improve the cell membrane permeability and bioavailability of the drug; enhance the pharmacological activity of the drug; increase the metabolic stability of the drug molecule, thereby prolonging the life of the drug. Action time. Due to the characteristics of strong electric absorption, high thermal stability, high metabolic stability, high lipophilicity and strong hydrophobicity, trifluoromethyl has better biologic...

Claims

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Application Information

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IPC IPC(8): C07D307/88
CPCC07D307/88
Inventor 蔡春陈婷婷
Owner NANJING UNIV OF SCI & TECH
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