Process for synthesizing alpha-bromoacetophenone compound

A technology of bromoacetophenone and synthesis method, which is applied in the field of synthesis of α-bromoacetophenone compounds, can solve problems such as acid gas corrosion equipment, complex operation, and environmental pollution, and achieve low bromination reagents and high product quality. The effect of high purity and simple operation

Inactive Publication Date: 2011-10-05
HUBEI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The above methods generally have the disadvantages of expensive bromination reagents used, complex operation, environmental pollution, acid gas corrosion equipment, or poor reaction zone selectivity.

Method used

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  • Process for synthesizing alpha-bromoacetophenone compound
  • Process for synthesizing alpha-bromoacetophenone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Add 36.7 g (220 mmol) of potassium bromate in 100 mL of water and 12.0 g (100 mmol) of acetophenone to a flask, stir, and slowly drop 22.9 g (220 mmol) of 25wt% sodium bisulfite solution into it, about half After adding in hours, control the temperature at 30℃ to react for 6 hours after dripping, cool to room temperature, filter, wash with ice water, recrystallize with n-hexane and dry to obtain white crystals 17.7g, yield 89%, mp48-50℃(lit .49-51°C).

Embodiment 2

[0027] Example 2: Add 36.7g (220mmol) of potassium bromate in 100mL of water and 12.0g (100mmol) of acetophenone to the flask, stir, and slowly drop 21.8g (220mmol) of 10wt% ammonium bisulfite solution into it. After the addition in half an hour, control the temperature at 40°C to react for 6 hours after the dropping, cool to room temperature, filter, wash with ice water, recrystallize and dry with n-hexane to obtain 15.7 g of white crystals, with a yield of 79%.

Embodiment 3

[0028] Example 3: Add 3.0 g (20 mmol) of sodium bromate in 100 mL of water and 1.3 g (9.1 mmol) of p-fluoroacetophenone into the flask, stir, and slowly drop 2.1 g (20 mmol) of 5wt% sulfurous acid into it Add sodium hydrogen solution in about half an hour. After dropping, control the temperature at 50°C to react for 9 hours, cool to room temperature, filter, wash with ice water, recrystallize and dry with cyclohexane to obtain 1.44g of white crystals, with a yield of 73%. mp46-48℃(lit.43-45℃).

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Abstract

The invention discloses a method for synthesizing alpha-bromo acetophenone compound, which comprises the steps: hydrosulphite solution is added into the mixture of substituted phenylethanone and bromate at the temperature of 30-90 DEG C, and the mixture is stirred to react for 2-9h, and then is cooled, filtered, washed and dried, so that the alpha-bromo acetophenone compound is obtained. The method also has the advantages that the product has high product purity, the price of bromide reagent is low, aqueous phase is solvent instead of organic solvent, the pollution is little, the operation issimple, and the method is suitable for mass production.

Description

Technical field [0001] The invention belongs to the technical field of organic chemistry, and specifically relates to a method for synthesizing an α-bromoacetophenone compound. Background technique [0002] α-Bromoacetophenone compounds are very important chemical intermediates and are widely used in medicine, dyes, pesticides and other industries. α-Bromoacetophenone compounds are generally prepared by bromination of corresponding acetophenone. Currently, there are mainly the following methods: [0003] 1. Jong, C.L; Hyun, J.P (Synthetic Communications, 2007, 37(1), 87-90.) Bromination reaction of acetophenone compounds with NBS. [0004] 2. Zhang, S.J.; Le, C.G. (Youji Huaxue, 2006, 26(2), 236-238) bromination of acetophenone compounds with tribromide-1-butyl-3-methylimidazole. [0005] 3. Kawano, T.; Kato, N. (Chemistry Letters, 2006, 35(3), 270-271.) et al. brominated acetophenone compounds with tetrabutylamine tribromide. [0006] 4. Satya, P.; Varinder, G.; Rajive, G.; Andre, L....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/80C07C45/63
Inventor 李焰袁振昌潘怡沛陈祖兴
Owner HUBEI UNIV
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