CN105218379A - The synthetic method of the chloro-5-bromaniline of a kind of 3- - Google Patents
The synthetic method of the chloro-5-bromaniline of a kind of 3- Download PDFInfo
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- CN105218379A CN105218379A CN201510722173.9A CN201510722173A CN105218379A CN 105218379 A CN105218379 A CN 105218379A CN 201510722173 A CN201510722173 A CN 201510722173A CN 105218379 A CN105218379 A CN 105218379A
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- chloro
- sulfonic acid
- nitrophenyl sulfonic
- bromine
- bromaniline
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Abstract
The invention discloses the synthetic method of the chloro-5-bromaniline of a kind of 3-, belong to technical field of organic synthesis.The present invention take Phenylsulfonic acid as starting material, first by adding concentrated nitric acid and manganese dioxide-catalyst generation p-nitrophenyl sulfonic acid, subsequently again by adding NBS, generate 2-bromine p-nitrophenyl sulfonic acid, afterwards by adding HCl, thus generate 2-chloro-6-bromine p-nitrophenyl sulfonic acid, then by adding CH
3cOOH solution, removes the Phenylsulfonic acid in 2-chloro-6-bromine p-nitrophenyl sulfonic acid, obtains the chloro-5-bromo nitrobenzene of 3-, finally by adding reduction Na
2s and Zn reduces, thus obtains the chloro-5-bromaniline of a kind of 3-obtained by the present invention.This examples prove, the present invention is simply easy to prepare, environment friendly and pollution-free, and not only facility investment is few, and without any pollution, and yield reaches more than 85%.
Description
Technical field
The invention discloses the synthetic method of the chloro-5-bromaniline of a kind of 3-, belong to technical field of organic synthesis.
Background technology
Bromaniline is weak yellow liquid or crystalline melt point (DEG C): 18.5, boiling point (DEG C): 251, relative density (water=1): 1.5800, flash-point (DEG C): >112, solvability: be slightly soluble in water, is dissolved in ethanol, ether.
Phenyl amines organism is a kind of purposes chemical intermediate widely, be widely used in the synthesis of medicine, dyestuff and other fine chemical products, phenyl amines can prepare amine benzenephosphonic acid class medicine in medical, for suppressing the formation of thrombus and preparing chloroquinoline thiazolidinedione as microbiotic etc., in dyestuff, be used for making multiple azoic dyestuff and many rings macromole dyestuff, in addition, also for the preparation of stopper, various sensitive materials, ion exchange resin.
The mode that the method for current industrial production bromaniline is still more traditional, there is the problems such as yield is low, purity is not high and seriously polluted, and production technique is comparatively complicated, is difficult to meet human wants in this traditional production method.Therefore, improve a kind of purity high, yield is high, and the synthesis technique preparing simple bromaniline is significantly.
Summary of the invention
The technical problem that the present invention mainly solves: there is process complexity, complex operation step and the lower problem of yield for the bromaniline synthetic method that current the present invention is traditional, provide the synthetic method of the chloro-5-bromaniline of a kind of 3-, the method take Phenylsulfonic acid as starting material, first by adding concentrated nitric acid and manganese dioxide-catalyst generation p-nitrophenyl sulfonic acid, subsequently again by adding NBS, generate 2-bromine p-nitrophenyl sulfonic acid, afterwards by adding HCl, thus generate 2-chloro-6-bromine p-nitrophenyl sulfonic acid, then by adding CH
3cOOH solution, remove in 2-chloro-6-bromine p-nitrophenyl sulfonic acid Phenylsulfonic acid, obtain the chloro-5-bromo nitrobenzene of 3-, finally by adding reduction Na
2s and Zn reduces, thus obtains the chloro-5-bromaniline of a kind of 3-obtained by the present invention.Not only operation is simple, and without any pollution, make yield obtain significant raising.
In order to achieve the above object, the synthetic route of the chloro-5-bromaniline of 3-of the present invention is:
The building-up process of the chloro-5-bromaniline of the 3-that the present invention relates to comprises the following steps:
(1) in the four-hole bottle of upper device agitator, prolong, dropping funnel and thermometer respectively, add 15 ~ 20g Phenylsulfonic acid, the mass concentration adding Phenylsulfonic acid quality 2 ~ 3 times afterwards is more successively the concentrated nitric acid of 88% and the Manganse Dioxide of 0.01 ~ 0.03 times, sealing is simultaneously warming up to 5 ~ 35 DEG C, pressure rises to 1.5 ~ 2MPa, and fully stir 25 ~ 45min, generate p-nitrophenyl sulfonic acid;
(2) in generation p-nitrophenyl sulfonic acid, add NBS, and stir simultaneously, wherein the add-on of NBS is 1 ~ 3 times of p-nitrophenyl sulfonic acid quality, when adding NBS, and control temperature scope is 0 ~ 30 DEG C, after question response terminates, and pours H into
2in O, separate organic layer, water layer C
2h
4cl
2extraction, washes organic layer again after merging organic layer, uses anhydrous Na afterwards
2sO
4carry out drying, suction filtration, obtain liquid 2-bromine p-nitrophenyl sulfonic acid;
(3) generating in the 2-bromine p-nitrophenyl sulfonic acid obtained, under the condition of normal temperature, the HCl solution that 50 ~ 70mL mass concentration is 25% is slowly dripped in dropping mode, carrying out heating in water bath to temperature after stirring is 90 ~ 95 DEG C, pressure rises to 2 ~ 2.5MPa, after reaction 45 ~ 50min, stops heating, uniform stirring 5 ~ 10min again, obtains 2-chloro-6-bromine p-nitrophenyl sulfonic acid after cooling;
(4) in the 2-obtained chloro-6-bromine p-nitrophenyl sulfonic acid, more slowly drip in dropping mode the CH that 35 ~ 55mL mass concentration is 30%
3cOOH solution, controlling preferred range is 10 ~ 20 DEG C, and pressure range is 1 ~ 2MPa, after reaction 10 ~ 15min, then increase optimum temperature range to 15 ~ 25 DEG C, pressure range to 1.5 ~ 2.5MPa, after fully stirring 25 ~ 30min afterwards, the chloro-5-bromo nitrobenzene of 3-can be obtained;
(5) four-hole bottle of difference device agitator, prolong, dropping funnel and a thermometer is got again, chloro-for the 3-obtained 5-bromo nitrobenzene is positioned over after in four-hole bottle, set temperature is 20 ~ 35 DEG C, and in whipping process, adds the Na of 3-chloro-5-bromo nitrobenzene quality 0.5 ~ 1.1 times successively
2the Zn of S and 0.3 ~ 0.5 times, keeps whipped state 15 ~ 20min, promote subsequently temperature be 35 ~ 45 DEG C to reacting end, separate organic layer, pass through C
2h
4cl
2extraction and underpressure distillation, post crystallization obtain the chloro-5-bromaniline of a kind of pale yellow crystals 3-.
The invention has the beneficial effects as follows: the present invention is simply easy to prepare, environment friendly and pollution-free, not only facility investment is few, and without any pollution, and yield significantly improves.
Embodiment
The building-up process of the chloro-5-bromaniline of a kind of 3-that the present invention relates to comprises the following steps:
First in the four-hole bottle of upper device agitator, prolong, dropping funnel and thermometer respectively, add 15 ~ 20g Phenylsulfonic acid, the mass concentration adding Phenylsulfonic acid quality 2 ~ 3 times afterwards is more successively the concentrated nitric acid of 88% and the Manganse Dioxide of 0.01 ~ 0.03 times, sealing is simultaneously warming up to 5 ~ 35 DEG C, pressure rises to 1.5 ~ 2MPa, and fully stir 25 ~ 45min, generate p-nitrophenyl sulfonic acid; Then, in generation p-nitrophenyl sulfonic acid, add NBS, and stir simultaneously, wherein the add-on of NBS is 1 ~ 3 times of p-nitrophenyl sulfonic acid quality, when adding NBS, and control temperature scope is 0 ~ 30 DEG C, after question response terminates, and pours H into
2in O, separate organic layer, water layer C
2h
4cl
2extraction, washes organic layer again after merging organic layer, uses anhydrous Na afterwards
2sO
4carry out drying, suction filtration, obtain liquid 2-bromine p-nitrophenyl sulfonic acid; Generating in the 2-bromine p-nitrophenyl sulfonic acid obtained subsequently, under the condition of normal temperature, the HCl solution that 50 ~ 70mL mass concentration is 25% is slowly dripped in dropping mode, carrying out heating in water bath to temperature after stirring is 90 ~ 95 DEG C, pressure rises to 2 ~ 2.5MPa, after reaction 45 ~ 50min, stops heating, uniform stirring 5 ~ 10min again, obtains 2-chloro-6-bromine p-nitrophenyl sulfonic acid after cooling; Afterwards in the 2-obtained chloro-6-bromine p-nitrophenyl sulfonic acid, more slowly drip in dropping mode the CH that 35 ~ 55mL mass concentration is 30%
3cOOH solution, controlling preferred range is 10 ~ 20 DEG C, and pressure range is 1 ~ 2MPa, after reaction 10 ~ 15min, then increase optimum temperature range to 15 ~ 25 DEG C, pressure range to 1.5 ~ 2.5MPa, after fully stirring 25 ~ 30min afterwards, the chloro-5-bromo nitrobenzene of 3-can be obtained; The last four-hole bottle getting difference device agitator, prolong, dropping funnel and a thermometer again, chloro-for the 3-obtained 5-bromo nitrobenzene is positioned over after in four-hole bottle, set temperature is 20 ~ 35 DEG C, and in whipping process, adds the Na of 3-chloro-5-bromo nitrobenzene quality 0.5 ~ 1.1 times successively
2the Zn of S and 0.3 ~ 0.5 times, keeps whipped state 15 ~ 20min, promote subsequently temperature be 35 ~ 45 DEG C to reacting end, separate organic layer, pass through C
2h
4cl
2extraction and underpressure distillation, post crystallization obtain the chloro-5-bromaniline of a kind of pale yellow crystals 3-.
Example 1
First in the four-hole bottle of upper device agitator, prolong, dropping funnel and thermometer respectively, add 15g Phenylsulfonic acid, the mass concentration adding Phenylsulfonic acid quality 2 times afterwards is more successively the concentrated nitric acid of 88% and the Manganse Dioxide of 0.01 times, sealing is simultaneously warming up to 5 DEG C, pressure rises to 1.5MPa, and fully stir 25min, generate p-nitrophenyl sulfonic acid; Then, in generation p-nitrophenyl sulfonic acid, add NBS, and stir simultaneously, wherein the add-on of NBS is 1 times of p-nitrophenyl sulfonic acid quality, when adding NBS, and control temperature scope is 0 DEG C, after question response terminates, and pours H into
2in O, separate organic layer, water layer C
2h
4cl
2extraction, washes organic layer again after merging organic layer, uses anhydrous Na afterwards
2sO
4carry out drying, suction filtration, obtain liquid 2-bromine p-nitrophenyl sulfonic acid; Generating in the 2-bromine p-nitrophenyl sulfonic acid obtained subsequently, under the condition of normal temperature, the HCl solution that 50mL mass concentration is 25% is slowly dripped in dropping mode, carrying out heating in water bath to temperature after stirring is 90 DEG C, pressure rises to 2MPa, after reaction 45min, stops heating, uniform stirring 5min again, obtains 2-chloro-6-bromine p-nitrophenyl sulfonic acid after cooling; Afterwards in the 2-obtained chloro-6-bromine p-nitrophenyl sulfonic acid, more slowly drip in dropping mode the CH that 35mL mass concentration is 30%
3cOOH solution, controlling preferred range is 10 DEG C, and pressure range is 1MPa, after reaction 10min, then increases optimum temperature range to 15 DEG C, and pressure range, to 1.5MPa, after fully stirring 25min afterwards, can obtain the chloro-5-bromo nitrobenzene of 3-; The last four-hole bottle getting difference device agitator, prolong, dropping funnel and a thermometer again, chloro-for the 3-obtained 5-bromo nitrobenzene is positioned over after in four-hole bottle, set temperature is 20 DEG C, and in whipping process, adds the Na of 3-chloro-5-bromo nitrobenzene quality 0.5 times successively
2the Zn of S and 0.3 times, keeps whipped state 15min, promote subsequently temperature be 35 DEG C to reacting end, separate organic layer, pass through C
2h
4cl
2extraction and underpressure distillation, post crystallization obtain the chloro-5-bromaniline of a kind of pale yellow crystals 3-.
This example is simple, and method is unique novel, and not only facility investment is few, and without any pollution, finally obtain 3-chloro-5-bromaniline pale yellow crystals 2.5g, yield is 85%.
Example 2
First in the four-hole bottle of upper device agitator, prolong, dropping funnel and thermometer respectively, add 18g Phenylsulfonic acid, the mass concentration adding Phenylsulfonic acid quality 2.5 times afterwards is more successively the concentrated nitric acid of 88% and the Manganse Dioxide of 0.02 times, sealing is simultaneously warming up to 25 DEG C, pressure rises to 1.8MPa, and fully stir 35min, generate p-nitrophenyl sulfonic acid; Then, in generation p-nitrophenyl sulfonic acid, add NBS, and stir simultaneously, wherein the add-on of NBS is 2 times of p-nitrophenyl sulfonic acid quality, when adding NBS, and control temperature scope is 25 DEG C, after question response terminates, and pours H into
2in O, separate organic layer, water layer C
2h
4cl
2extraction, washes organic layer again after merging organic layer, uses anhydrous Na afterwards
2sO
4carry out drying, suction filtration, obtain liquid 2-bromine p-nitrophenyl sulfonic acid; Generating in the 2-bromine p-nitrophenyl sulfonic acid obtained subsequently, under the condition of normal temperature, the HCl solution that 60mL mass concentration is 25% is slowly dripped in dropping mode, carrying out heating in water bath to temperature after stirring is 93 DEG C, pressure rises to 2.3MPa, after reaction 48min, stops heating, uniform stirring 8min again, obtains 2-chloro-6-bromine p-nitrophenyl sulfonic acid after cooling; Afterwards in the 2-obtained chloro-6-bromine p-nitrophenyl sulfonic acid, more slowly drip in dropping mode the CH that 45mL mass concentration is 30%
3cOOH solution, controlling preferred range is 15 DEG C, and pressure range is 1.5MPa, after reaction 13min, then increases optimum temperature range to 20 DEG C, and pressure range, to 2MPa, after fully stirring 28min afterwards, can obtain the chloro-5-bromo nitrobenzene of 3-; The last four-hole bottle getting difference device agitator, prolong, dropping funnel and a thermometer again, chloro-for the 3-obtained 5-bromo nitrobenzene is positioned over after in four-hole bottle, set temperature is 30 DEG C, and in whipping process, adds the Na of 3-chloro-5-bromo nitrobenzene quality 0.9 times successively
2the Zn of S and 0.4 times, keeps whipped state 18min, promoting temperature 40 DEG C subsequently to reacting end, separating organic layer, passing through C
2h
4cl
2extraction and underpressure distillation, post crystallization obtain the chloro-5-bromaniline of a kind of pale yellow crystals 3-.
This example is simple, and method is unique novel, and not only facility investment is few, and without any pollution, finally obtain 3-chloro-5-bromaniline pale yellow crystals 3.5g, yield is 88%.
Example 3
First in the four-hole bottle of upper device agitator, prolong, dropping funnel and thermometer respectively, add 20g Phenylsulfonic acid, the mass concentration adding Phenylsulfonic acid quality 2 ~ 3 times afterwards is more successively the concentrated nitric acid of 88% and the Manganse Dioxide of 0.03 times, sealing is simultaneously warming up to 35 DEG C, pressure rises to 2MPa, and fully stir 45min, generate p-nitrophenyl sulfonic acid; Then, in generation p-nitrophenyl sulfonic acid, add NBS, and stir simultaneously, wherein the add-on of NBS is 3 times of p-nitrophenyl sulfonic acid quality, when adding NBS, and control temperature scope is 30 DEG C, after question response terminates, and pours H into
2in O, separate organic layer, water layer C
2h
4cl
2extraction, washes organic layer again after merging organic layer, uses anhydrous Na afterwards
2sO
4carry out drying, suction filtration, obtain liquid 2-bromine p-nitrophenyl sulfonic acid; Generating in the 2-bromine p-nitrophenyl sulfonic acid obtained subsequently, under the condition of normal temperature, the HCl solution that 70mL mass concentration is 25% is slowly dripped in dropping mode, carrying out heating in water bath to temperature after stirring is 95 DEG C, pressure rises to 2.5MPa, after reaction 50min, stops heating, uniform stirring 10min again, obtains 2-chloro-6-bromine p-nitrophenyl sulfonic acid after cooling; Afterwards in the 2-obtained chloro-6-bromine p-nitrophenyl sulfonic acid, more slowly drip in dropping mode the CH that 55mL mass concentration is 30%
3cOOH solution, controlling preferred range is 20 DEG C, and pressure range is 2MPa, after reaction 15min, then increases optimum temperature range to 25 DEG C, and pressure range, to 2.5MPa, after fully stirring 30min afterwards, can obtain the chloro-5-bromo nitrobenzene of 3-; The last four-hole bottle getting difference device agitator, prolong, dropping funnel and a thermometer again, chloro-for the 3-obtained 5-bromo nitrobenzene is positioned over after in four-hole bottle, set temperature is 35 DEG C, and in whipping process, adds the Na of 3-chloro-5-bromo nitrobenzene quality 1.1 times successively
2the Zn of S and 0.5 times, keeps whipped state 20min, promote subsequently temperature be 45 DEG C to reacting end, separate organic layer, pass through C
2h
4cl
2extraction and underpressure distillation, post crystallization obtain the chloro-5-bromaniline of a kind of pale yellow crystals 3-.
This example is simple, and method is unique novel, and not only facility investment is few, and without any pollution, finally obtain 3-chloro-5-bromaniline pale yellow crystals 4.5g, yield is 90%.
Claims (1)
1. a synthetic method for the chloro-5-bromaniline of 3-, is characterized in that concrete synthesis step is:
(1) in the four-hole bottle of upper device agitator, prolong, dropping funnel and thermometer respectively, add 15 ~ 20g Phenylsulfonic acid, the mass concentration adding Phenylsulfonic acid quality 2 ~ 3 times afterwards is more successively the concentrated nitric acid of 88% and the Manganse Dioxide of 0.01 ~ 0.03 times, sealing is simultaneously warming up to 5 ~ 35 DEG C, pressure rises to 1.5 ~ 2MPa, and fully stir 25 ~ 45min, generate p-nitrophenyl sulfonic acid;
(2) in generation p-nitrophenyl sulfonic acid, add NBS, and stir simultaneously, wherein the add-on of NBS is 1 ~ 3 times of p-nitrophenyl sulfonic acid quality, when adding NBS, and control temperature scope is 0 ~ 30 DEG C, after question response terminates, and pours H into
2in O, separate organic layer, water layer C
2h
4cl
2extraction, washes organic layer again after merging organic layer, uses anhydrous Na afterwards
2sO
4carry out drying, suction filtration, obtain liquid 2-bromine p-nitrophenyl sulfonic acid;
(3) generating in the 2-bromine p-nitrophenyl sulfonic acid obtained, under the condition of normal temperature, the HCl solution that 50 ~ 70mL mass concentration is 25% is slowly dripped in dropping mode, carrying out heating in water bath to temperature after stirring is 90 ~ 95 DEG C, pressure rises to 2 ~ 2.5MPa, after reaction 45 ~ 50min, stops heating, uniform stirring 5 ~ 10min again, obtains 2-chloro-6-bromine p-nitrophenyl sulfonic acid after cooling;
(4) in the 2-obtained chloro-6-bromine p-nitrophenyl sulfonic acid, more slowly drip in dropping mode the CH that 35 ~ 55mL mass concentration is 30%
3cOOH solution, controlling preferred range is 10 ~ 20 DEG C, and pressure range is 1 ~ 2MPa, after reaction 10 ~ 15min, then increase optimum temperature range to 15 ~ 25 DEG C, pressure range to 1.5 ~ 2.5MPa, after fully stirring 25 ~ 30min afterwards, the chloro-5-bromo nitrobenzene of 3-can be obtained;
(5) four-hole bottle of difference device agitator, prolong, dropping funnel and a thermometer is got again, chloro-for the 3-obtained 5-bromo nitrobenzene is positioned over after in four-hole bottle, set temperature is 20 ~ 35 DEG C, and in whipping process, adds the Na of 3-chloro-5-bromo nitrobenzene quality 0.5 ~ 1.1 times successively
2the Zn of S and 0.3 ~ 0.5 times, keeps whipped state 15 ~ 20min, promote subsequently temperature be 35 ~ 45 DEG C to reacting end, separate organic layer, pass through C
2h
4cl
2extraction and underpressure distillation, post crystallization obtain the chloro-5-bromaniline of a kind of pale yellow crystals 3-.
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1264820A1 (en) * | 2000-03-14 | 2002-12-11 | Fujisawa Pharmaceutical Co., Ltd. | Novel amide compounds |
US20100093703A1 (en) * | 2007-02-16 | 2010-04-15 | Boehringer Ingelheim International Gmbh | Substituted arylsulphonylglycines, the preparation thereof and the use thereof as pharmaceutical compositions |
CN101735023A (en) * | 2008-11-24 | 2010-06-16 | 联化科技股份有限公司 | Method for preparing 3-bromo-5-chlorophenol |
CN102146022A (en) * | 2010-02-05 | 2011-08-10 | 中国中化股份有限公司 | Method for preparing 3-chlorine-5-bromophenol |
-
2015
- 2015-10-31 CN CN201510722173.9A patent/CN105218379A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1264820A1 (en) * | 2000-03-14 | 2002-12-11 | Fujisawa Pharmaceutical Co., Ltd. | Novel amide compounds |
US20100093703A1 (en) * | 2007-02-16 | 2010-04-15 | Boehringer Ingelheim International Gmbh | Substituted arylsulphonylglycines, the preparation thereof and the use thereof as pharmaceutical compositions |
CN101735023A (en) * | 2008-11-24 | 2010-06-16 | 联化科技股份有限公司 | Method for preparing 3-bromo-5-chlorophenol |
CN102146022A (en) * | 2010-02-05 | 2011-08-10 | 中国中化股份有限公司 | Method for preparing 3-chlorine-5-bromophenol |
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