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Method for preparing p-tert-butyl o-nitrothiophenol

A technology of nitrothiophenol and tert-butyl o-o, which is applied in the field of synthesis of chemical intermediates, and can solve problems such as difficulty in obtaining, high cost of raw materials, and long reaction routes

Inactive Publication Date: 2010-06-09
北京金源化学集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] This method is currently the main method for preparing p-tert-butyl-o-nitrothiophenol, but this method also has problems such as high raw material cost, difficulty in obtaining, long reaction route, difficult reaction conditions, and low yield. Based on reducing the reaction cost , in consideration of improving the reaction yield and improving the source of raw materials, the inventor has developed a new synthesis process for p-tert-butyl-o-nitrothiophenol

Method used

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  • Method for preparing p-tert-butyl o-nitrothiophenol

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Effect test

Embodiment 1

[0014] Add 10 moles of o-nitrothiophenol to the reactor, maintain zero temperature and keep stirring, slowly add 300 grams of BF 3 / H 3 PO 4 Composite catalyst and 11 moles of isobutene. The reaction time is 4 hours. After completion, the temperature is raised to 70-75° C., and the stirring reaction is continued for 2 hours. After cooling to room temperature, the organic phase and the catalyst phase were separated, and the organic phase was separated and dissolved in 500 ml of toluene. The toluene solution was washed 4 times with 1000 ml of water, and dried over anhydrous magnesium sulfate. The toluene was removed by rotary evaporation, and the residue was distilled under reduced pressure (80-100° C. / 1 mmHg) to obtain the product p-tert-butyl-o-nitrothiophenol with a yield of 70%.

Embodiment 2

[0016] Add 50 grams of o-nitrothiophenol in 250 milliliters of stirring reactors, 10 grams of strongly acidic cationic resins (macroporous styrene-divinylbenzenesulfonic acid type cationic exchange resins), decompress to 200 millimeters of mercury, system Maintaining the reaction temperature at 120°C, 180 ml of tert-butyl methyl ether was added to the reaction kettle within 1 hour. After the completion of the insulation reaction for 2h. Cool to room temperature, add 100ml of dichloromethane to dissolve, wash the organic phase with 20ml of water 4 times, and dry over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation to obtain a crude product of p-tert-butyl-o-nitrothiophenol, and the yield of the crude product was 68%.

Embodiment 3

[0018] Add 10 moles of 4,4'-di-tert-butyl-2,2'-dinitrodiphenyl sulfide to the reactor, maintain zero temperature and keep stirring, slowly add 150 grams of AlCl 3 , 620 g (10.9 moles) of isobutyl chloride. After completion, the temperature was raised to 0-10 degrees and the reaction was stirred for 2 hours. The temperature was raised to 70-75 degrees, and the stirring reaction was continued for 2h. After cooling to room temperature, 500 ml of dichloromethane was added and extracted with 100 ml. The organic phases were combined, washed 4 times with 1000 ml of water, and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation to obtain the crude product of 4,4'-di-tert-butyl-2,2'-dinitrodiphenylsulfide, and the yield of the crude product was 78%.

[0019] Add 20 milliliters of methanol, 6 mmoles of 4,4'-di-tert-butyl-2,2'-dinitrodiphenylsulfide in the reaction flask, 2 Stir and heat to reflux under atmosphere, add dropwise a solution of 0.96 g (...

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Abstract

The invention relates to the synthesis field of chemical intermediates and discloses a method for directly preparing p-tert-butyl o-nitrothiophenol. In the method, with o-nitrothiophenol or 2,2'-binitro diphenyl disulfide as the raw material, the p-tert-butyl o-nitrothiophenol and the derivatives thereof are obtained through tert-butylation reaction. The method is characterized by easily obtained raw materials, short reaction route, higher relative reaction yield and easy realization of large-scale production.

Description

technical field [0001] The invention relates to the field of synthesis of chemical intermediates, and is a method for directly preparing p-tert-butyl-o-nitrothiophenol. The method uses o-nitrothiophenol or 2,2'-dinitrodiphenyldisulfide as the Raw materials, after tert-butylation reaction, get p-tert-butyl-o-nitrothiophenol. Background technique [0002] p-tert-butyl-o-nitrothiophenol is an important synthetic raw material, mainly used in many fields such as pharmaceutical intermediates, photosensitive materials, electrochromic display materials, electrolytic polymerization monomers and extractant intermediates. And its preparation method is few, mainly contains the synthetic route of document [Journal of Organic Chemistry, 1980,45 (21), 4216] report, is raw material with p-tert-butyl-o-nitrophenol, through a series of complicated functional conversion, will The phenolic hydroxyl group is converted into a phenolic mercapto group, and the specific reaction is shown in the fig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/09C07C319/12
Inventor 张和平陈朝晖邱明建张雅丽于淑利李海滨赵磊刘婧于冰何琼
Owner 北京金源化学集团有限公司
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