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Friedel-Crafts acylation reaction catalyzed trifluoroacetic acid

A technology of trifluoroacetic acid and trifluoroacetic anhydride, which is applied in the field of Friedel-Crafts acylation reaction, can solve the problems that catalysts cannot be recycled well, environmental pollution, a large amount of aluminum salt waste liquid, etc., and achieves good application prospects and economy. high effect

Inactive Publication Date: 2017-12-01
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are many disadvantages in this kind of reaction: 1) the equivalent catalyst is used; 2) using acid chloride as the acylation raw material, a large amount of HCl gas will be generated in the post-treatment process, which will cause environmental pollution; 3) a large amount of HCl gas will be generated in the reaction process. aluminum salt waste
The disadvantages of the reaction system are: 1) the catalyst cannot be recycled well; 2) a large amount of water needs to be used to remove the catalyst and the corresponding by-products in the post-treatment process

Method used

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  • Friedel-Crafts acylation reaction catalyzed trifluoroacetic acid
  • Friedel-Crafts acylation reaction catalyzed trifluoroacetic acid
  • Friedel-Crafts acylation reaction catalyzed trifluoroacetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] By screening the reaction conditions:

[0019] entry

equiv of 2a

Solvent

Yield b / %

1

2

TFA (1mL)

100

2

2

50:50 TFA / DCM

69

3

2

80:20 TFA / DCM

95

4

2

50:50 TFA / HFIP

14

5

2

80:20 TFA / HFIP

44

6

2

TFA (0.5mL)

95

7

2

TFA (0.8mL)

100(95 c )

8

1.2

TFA (0.8mL)

84

9

1.5

TFA (0.8mL)

96

[0020] The best reaction conditions were obtained, that is, at room temperature, anisole (0.75mmol) and acetic anhydride (1.5mmol) were reacted in trifluoroacetic acid (0.8mL) for 1.5h to obtain the target product with a conversion rate of 100%. The applicable range and conversion rate of other substrates are as follows: figure 2 shown.

[0021]

Embodiment 2

[0023] By screening the reaction conditions:

[0024] entry

equiv of 2a

Solvent

Yield b / %

1

1

TFA (1mL)

53

2

1.5

TFA (1mL)

62

3

2

TFA (1mL)

50

4

3

TFA (1mL)

62

5

1.5

TFA (2mL)

78(65 c )

6

1.5

TFA (3mL)

71

[0025] The optimal reaction conditions were obtained, that is, at 100°C, isobutylbenzene (0.75mmol) and acetic anhydride (1.125mmol) were reacted in trifluoroacetic acid (2mL) for 56h to obtain the target product with a conversion rate of 78%. The applicable range and conversion rate of other substrates are as follows: image 3 shown.

[0026]

Embodiment 3

[0028] By screening the reaction conditions:

[0029] entry

equiv of 1a

Solvent

Yield b / %

1

1

Trifluoroacetate

48

2

1.2

Trifluoroacetate

95

3

1.5

Trifluoroacetate

98

4

2

Trifluoroacetate

98

[0030] The best reaction conditions were obtained, that is, at room temperature, anisole (1.125mmol), benzoic acid (0.75mmol), and trifluoroacetic anhydride (1.5mmol) were reacted in trifluoroacetic acid (0.8mL) for 12h to obtain the target Product, 98% conversion. The applicable range and conversion rate of other substrates are as follows: Figure 4 shown.

[0031]

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PUM

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Abstract

The invention relates to a Friedel-Crafts acylation reaction catalyzed trifluoroacetic acid. According to the invention, acid anhydride or carboxylic acid reacts with an aromatic hydrocarbon compound under the catalysis of trifluoroacetic acid and / or trifluoroacetic anhydride to produce a Friedel-Crafts acylation product. The catalyst used in the invention can be recycled, and no extra solvent is needed; the carboxylic acid or acid anhydride is used as a starting material and preparation of acyl chloride from the starting material is not needed; water treatment is not needed in subsequent reaction process; the atom economy of the reaction is high; little or no waste is produced; and good prospects are obtained.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a Friedel-Crafts acylation reaction catalyzed by trifluoroacetic acid. Background technique [0002] The Friedel-Crafts acylation reaction is a very important reaction in the synthesis of materials and drugs. In the traditional Friedel-Crafts acylation reaction, Lewis acid is usually used to catalyze the Friedel-Crafts reaction of acid chlorides and aromatic hydrocarbons. However, there are many disadvantages in this kind of reaction: 1) the equivalent catalyst is used; 2) using acid chloride as the acylation raw material, a large amount of HCl gas will be generated in the post-treatment process, which will cause environmental pollution; 3) a large amount of HCl gas will be generated in the reaction process. aluminum salt waste. Subsequently, chemists developed the so-called "green" Friedel-Crafts acylation reaction, using heteropolyacids or non-metallic Lewis acids as catalysts t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/46C07C49/84C07C49/76C07C49/67C07B41/06
CPCY02P20/582C07C45/46C07B41/06C07C49/84C07C49/76C07C49/67
Inventor 胥波刘广昌
Owner DONGHUA UNIV
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