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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: 2009-06-24
HUBEI UNIV
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  • Abstract
  • Description
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  • 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

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Experimental program
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Embodiment 1

[0026] Embodiment one: add 100mL aqueous solution of 36.7g (220mmol) potassium bromate and 12.0g (100mmol) acetophenone in the flask, stir, slowly add dropwise to wherein containing 22.9g (220mmol) 25wt% sodium bisulfite solution, about half After the addition was completed within 1 hour, the reaction temperature was controlled at 30°C for 6 hours after dropping, cooled to room temperature, filtered, washed with ice water, recrystallized and dried with n-hexane to obtain 17.7g of white crystals, the yield was 89%, m.p.48-50°C (lit. .49-51°C).

Embodiment 2

[0027] Embodiment two: add 100mL aqueous solution of 36.7g (220mmol) Potassium Bromate and 12.0g (100mmol) acetophenone in the flask, stir, slowly add dropwise the 10wt% ammonium bisulfite solution containing 21.8g (220mmol) therein, about The addition was completed in half an hour, and after the dropping, the temperature was controlled at 40°C for 6 hours, cooled to room temperature, filtered, washed with ice water, recrystallized and dried with n-hexane to obtain 15.7 g of white crystals, with a yield of 79%.

Embodiment 3

[0028] Embodiment three: add 100mL aqueous solution of 3.0g (20mmol) sodium bromate and 1.3g (9.1mmol) p-fluoroacetophenone in the flask, stir, slowly add dropwise the 5wt% sulfurous acid containing 2.1g (20mmol) wherein Sodium hydrogen solution was added in about half an hour. After dropping, the temperature was controlled at 50°C for 9 hours, cooled to room temperature, filtered, washed with ice water, recrystallized and dried with cyclohexane to obtain 1.44 g of white crystals, with a yield of 73%. m.p. 46-48°C (lit. 43-45°C).

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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 is simple, and the method is suitable for mass production.

Description

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

Claims

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Application Information

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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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