CN101774953A - Preparation method for substituted diphenyl sulfide - Google Patents
Preparation method for substituted diphenyl sulfide Download PDFInfo
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- CN101774953A CN101774953A CN201010101517A CN201010101517A CN101774953A CN 101774953 A CN101774953 A CN 101774953A CN 201010101517 A CN201010101517 A CN 201010101517A CN 201010101517 A CN201010101517 A CN 201010101517A CN 101774953 A CN101774953 A CN 101774953A
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- diphenyl sulfide
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- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 150000001555 benzenes Chemical class 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 9
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims abstract description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims abstract description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 5
- 229910015900 BF3 Inorganic materials 0.000 claims abstract description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 3
- 239000012046 mixed solvent Substances 0.000 claims abstract description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 12
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- -1 diphenylamine disulfide Chemical class 0.000 claims description 4
- 238000012423 maintenance Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000012188 paraffin wax Substances 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 4
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 abstract 1
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical class ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- RKMZTRDJSKGOCM-UHFFFAOYSA-N 1-chloro-4-phenylsulfanylbenzene Chemical compound C1=CC(Cl)=CC=C1SC1=CC=CC=C1 RKMZTRDJSKGOCM-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical group ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- MJEPOVIWHVRBIT-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)sulfanylbenzene Chemical compound C1=CC(Cl)=CC=C1SC1=CC=C(Cl)C=C1 MJEPOVIWHVRBIT-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical class IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Abstract
The invention relates to a synthesis method for organic compound, in particular to a preparation method for substituted diphenyl sulfide, belonging to the technical field of organic chemical substance preparation. Under the existence of Lewis acid catalyst, reaction temperature is controlled to be negative 10 DEG C to 70 DEG C to enable substituted benzene sulfenyl chloride and substituted benzene to take place Friedel-Crafts reaction in chloralkane solvent to generate substituted diphenyl sulfide. The used chloralkane solvent is mixed solvent formed by one or more of monochloromethane, dichloromethane, chloroform, carbon tetrachloride, dichloroethane and tetrachloroethane. The used catalyst is mixed catalyst formed by one or more of anhydrous ferric chloride, anhydrous aluminum chloride, titanium tetrachloride and anhydrous boron trifluoride. The invention has the advantages that the price of the raw materials is low, the synthesis reaction is mild and stable, the conversion rate of the raw materials is high, the product selectivity is good, the product can be easily separated from solvent, the product yield is high and the like.
Description
Technical field:
The invention belongs to the organic chemicals preparing technical field, relate to a kind of preparation method of new synthetic method, particularly a kind of substituted diphenyl sulfide of organic compound material.
Background technology:
As everyone knows, fragrance sulfide especially substituted diphenyl sulfide is the organism that a class has pharmaceutical activity, it is widely used in various treatments field as pharmaceutical intermediate, such as diabetes, anti-infective, immunity, alzheimer's disease and parkinsonism etc., modern medicine preparing technical field particularly, substituted diphenyl sulfide has more development prospect widely.At present, many both at home and abroad scholars and unit carry out the research and the experiment of this respect, particularly to the preparation of substituted diphenyl sulfide or synthetic technology carrying out in various degree a large amount of discussion and research and development; For example the people such as Joseph Levy of AP Oil company take at mineral alkali K in the U.S. Pat 3254125 of application in 1966
2CO
3Synthesized the chloro diphenyl sulfide according to following reaction formula under the existence condition:
Experimental results show that, when this method prepares the chloro diphenyl sulfide, its long reaction time, yield is on the low side less than 50%, can not obtain target product with high purity by ordinary methods such as crystallizations, and have only when strong electron-withdrawing group is arranged on the aromatic nucleus above-mentioned reaction just can carry out.People such as the Wang Zhi of Chinese Academy of Sciences duty is arranged again in the technology in the 462-465 page or leaf record of " organic chemistry " the 8th phase in 1988, in no divide power slot be that raw material uses methylene dichloride to make chlorizating agent to have synthesized 4-chloro diphenyl sulfide with 35% yield with the diphenyl sulfide, obtained simultaneously 60.1% 4,4 '-dichloro-diphenyl sulfide, this method can use this variation route of electrolysis to synthesize substituted diphenyl sulfide, its shortcoming is that the selectivity of target product is low, and the task of separate targets product is heavy and will realize that suitability for industrialized production has certain difficulty.Also have people such as Yugen Zhang in the technical scheme in the 3495th page of record of " Organic Letters " the 9th phase in 2007, in the DMF solvent, under Ni class catalyzer and potassium tert.-butoxide condition, successfully synthesize substituted diphenyl sulfide by following route:
X＝Cl，Br，I
The shortcoming of this method is that to select the phenyl-iodide compounds for use be raw material, and it costs an arm and a leg, and is difficult to the synthetic target product of high yield under the reaction process complexity, normal condition.End is got up, and have not yet to see the technological process of ideal substituted diphenyl sulfide preparation, and existing preparation or synthesis technique ubiquity the reaction process complexity, and product yield is low, and the cost height is difficult to obtain the target product of high yield under the normal condition.
Summary of the invention:
The objective of the invention is to overcome the shortcoming that prior art exists, seek to provide a kind of new preparation process of substituted diphenyl sulfide, this method is under solvent action, and the substituted diphenyl sulfide product is prepared in control reaction temperature and the chemosynthesis of catalyzer condition.
To achieve these goals, the present invention is under the lewis acid catalyst existence condition, and control reaction temperature is-10 ℃～70 ℃, makes substituted benzene time SULPHURYL CHLORIDE generate substituted diphenyl sulfide with substituted benzene generation Friedel-Crafts reaction in chlorinated paraffin solvent; Earlier in the containers such as flask that prolong and chlorine inlet tube are housed, add substituted diphenylamine disulfide and tetracol phenixin by weight percentage, dissolve the chlorine that slow feeding vitriol oil drying is crossed in back 3 hours fully in stirring and also be no more than 20 ℃ with water-bath maintenance reaction solution internal temperature during the course, keep 2 hours stopped reaction of this temperature stirring then; Normal pressure steams tetracol phenixin, and vacuum distilling obtains the red benzene time SULPHURYL CHLORIDE of boiling point 40-49 ℃/2mmHg; Add substituted benzene, chloroparaffin and lewis acid catalyst again in flask by weight percentage, the interior temperature of water-bath maintenance flask is 25 ℃ under the agitation condition, drips the inferior SULPHURYL CHLORIDE of the substituted benzene that has prepared then 1 hour; Dropwise under this temperature, to continue to stir and finished reaction in 2 hours; Then reaction mixture is slowly poured in the mixture of ice and water of stirring into layering, anhydrous magnesium sulfate drying; Chloroparaffin and unreacted substituted benzene are removed in air distillation; Last vacuum distilling is collected target fraction and is obtained colourless liquid substituted diphenyl sulfide product; The equation general formula of its Fu Ke chemical reaction is:
Wherein R is a kind of among H, C1～C4 alkyl, C1～C4 alkoxyl group, ethanoyl, propionyl, F, Cl or the Br; R ' is a kind of among H, C1～C4 alkyl, C1～C4 alkoxyl group, ethanoyl, propionyl, F, Cl or the Br.
The selected chlorinated paraffin solvent of the present invention is a mixed solvent, belongs to one or more the mixing in monochloro methane, methylene dichloride, chloroform, tetracol phenixin, ethylene dichloride and the tetrachloroethane; Temperature of reaction is-10 ℃～70 ℃, more preferably 0 ℃～40 ℃, is preferably 20～30 ℃; Selected catalyzer is one or more the mixing in FERRIC CHLORIDE ANHYDROUS, aluminum trichloride (anhydrous), titanium tetrachloride and the anhydrous boron trifluoride.
The present invention compared with prior art has that cost of material is low, building-up reactions is gentle steadily, feed stock conversion is high, product selectivity good, product is easy to characteristics such as separation, product yield height from solvent.
Embodiment:
Below by embodiment the present invention is further described.The substituted diphenyl sulfide that substituted diphenyl sulfide involved in the present invention is not limited only among the embodiment to be comprised.
Synthesizing of embodiment 1:4-fluorine diphenyl sulfide
In the 1000mL flask that prolong (the alkali lye device of termination monochlor(in)ate calcium drying tube and absorption chlorine on the prolong) and chlorine inlet tube are housed, add diphenyl disulfide (88g earlier, 0.4mol), the 300mL tetracol phenixin, open magnetic agitation, treat to dissolve fully the back and slowly fed the dry chlorine of crossing of the vitriol oil 3 hours; In this process, keep the reaction solution internal temperature to be no more than 20 ℃, keep this temperature to stir 2 hours stopped reaction then with water-bath; Air distillation tetracol phenixin, vacuum distilling obtain the red benzene time SULPHURYL CHLORIDE 51g of boiling point 40-49 ℃/2mmHg, yield 88%; Add 100mL fluorobenzene and 100mL tetracol phenixin again in the 500mL flask, (16g 0.12mol), starts stirring to aluminum trichloride (anhydrous), and it is 25 ℃ that water-bath keeps the interior temperature of bottle, and (11.3g 0.1mol), dripped 1 hour to drip the benzene time SULPHURYL CHLORIDE that has prepared then; Dropwise under this temperature, to continue to stir and finished reaction in 2 hours; Then reaction mixture is slowly poured in the 200g mixture of ice and water of stirring into layering, anhydrous magnesium sulfate drying; Tetracol phenixin and unreacted fluorobenzene are removed in air distillation; The cut that 160-165 ℃/266Pa of boiling point is collected in last vacuum distilling obtains colourless liquid 18g, and yield 82% is 4-fluorine diphenyl sulfide product;
1HNMR (400M, CDCl
3, TMS): δ=7.01 (ddt, J=8.8Hz, 2H), 7.20-7.22 (m, 1H), 7.23-7.29 (m, 4H), 7.36 (ddt, 8.8Hz, 2H).
Synthesizing of embodiment 2:4-chloro diphenyl sulfide
Earlier according to corresponding steps among the embodiment 1 and the synthetic 4-chlorobenzene time SULPHURYL CHLORIDE of mode; Add 100mL benzene and 100mL tetracol phenixin again in the 500mL flask, (16g 0.12mol), starts stirring to aluminum trichloride (anhydrous), and water-bath keeps 25 ℃ of the interior temperature of bottle, and (18g 0.1mol), dripped 2 hours to drip the 4-chlorobenzene time SULPHURYL CHLORIDE that has prepared then; Dropwise under 25 ℃ of temperature, to continue to stir and finished reaction in 2 hours; Then reaction mixture is slowly poured in the 200g mixture of ice and water of stirring into layering, anhydrous magnesium sulfate drying; The cut that tetracol phenixin and 190-196 ℃/266Pa of unreacted benzene final vacuum distillation collection boiling point are removed in last air distillation obtains colourless liquid 19.5g, and yield 74% is 4-chloro diphenyl sulfide product;
1HNMR (400M, CDCl
3, TMS): δ=7.03 (ddt, J=8.8Hz, 2H), 7.22-7.24 (m, 1H), 7.25-7.29 (m, 4H), 7.38 (ddt, 8.8Hz, 2H).
Synthesizing of embodiment 3:4-chloro-4 '-methyldiphenyl thioether
Earlier according to corresponding steps among the embodiment 1 and the synthetic 4-chlorobenzene time SULPHURYL CHLORIDE of mode; Add 100mL toluene and 100mL ethylene dichloride again in the 500mL flask, (16g 0.12mol), starts stirring to Zinc Chloride Anhydrous, and water-bath keeps 25 ℃ of the interior temperature of bottle, and (18g 0.1mol), dripped 2 hours to drip the 4-chlorobenzene time SULPHURYL CHLORIDE that has prepared then; Dropwise under 25 ℃ of temperature, to continue to stir and finished reaction in 2 hours; Then reaction mixture is slowly poured in the 200g mixture of ice and water of stirring into layering, anhydrous magnesium sulfate drying; The cut that tetracol phenixin and 183-185 ℃/266Pa of unreacted toluene final vacuum distillation collection boiling point are removed in last air distillation obtains colourless liquid 16.7g, and yield 71% is 4-chloro-4 '-methyldiphenyl thioether product;
1HNMR (400M, CDCl
3, TMS): δ=7.12-7.29 (m, 8H), 1.56 (s, 3H).
Claims (2)
1. the preparation method of a substituted diphenyl sulfide, it is characterized in that under the lewis acid catalyst existence condition, control reaction temperature is-10 ℃～70 ℃, makes substituted benzene time SULPHURYL CHLORIDE generate substituted diphenyl sulfide with substituted benzene generation Friedel-Crafts reaction in chlorinated paraffin solvent; Earlier in the flask that prolong and chlorine inlet tube are housed, add substituted diphenylamine disulfide and tetracol phenixin by weight percentage, dissolve the chlorine that slow feeding vitriol oil drying is crossed in back 3 hours fully in stirring and also be no more than 20 ℃ with water-bath maintenance reaction solution internal temperature during the course, keep 2 hours stopped reaction of this temperature stirring then; Normal pressure steams tetracol phenixin, and vacuum distilling obtains the red benzene time SULPHURYL CHLORIDE of boiling point 40-49 ℃/2mmHg; Add substituted benzene, chloroparaffin and lewis acid catalyst again in flask by weight percentage, the interior temperature of water-bath maintenance flask is 25 ℃ under the agitation condition, drips the inferior SULPHURYL CHLORIDE of the substituted benzene that has prepared then 1 hour; Dropwise under this temperature, to continue to stir and finished reaction in 2 hours; Then reaction mixture is slowly poured in the mixture of ice and water of stirring into layering, anhydrous magnesium sulfate drying; Chloroparaffin and unreacted substituted benzene are removed in air distillation; Last vacuum distilling is collected target fraction and is obtained colourless liquid substituted diphenyl sulfide product; The equation general formula of its Fu Ke chemical reaction is:
Wherein R is a kind of among H, C1～C4 alkyl, C1～C4 alkoxyl group, ethanoyl, propionyl, F, Cl or the Br; R ' is a kind of among H, C1～C4 alkyl, C1～C4 alkoxyl group, ethanoyl, propionyl, F, Cl or the Br.
2. the preparation method of substituted diphenyl sulfide according to claim 1, it is characterized in that selected chlorinated paraffin solvent is a mixed solvent, belong to one or more the mixing in monochloro methane, methylene dichloride, chloroform, tetracol phenixin, ethylene dichloride and the tetrachloroethane; Selected catalyzer is one or more the mixing in FERRIC CHLORIDE ANHYDROUS, aluminum trichloride (anhydrous), titanium tetrachloride and the anhydrous boron trifluoride.
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| CN201010101517A CN101774953A (en) | 2010-01-21 | 2010-01-21 | Preparation method for substituted diphenyl sulfide |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351622A (en) * | 2011-08-19 | 2012-02-15 | 浙江大学 | Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt |
| CN102516139A (en) * | 2011-11-02 | 2012-06-27 | 浙江工业大学 | Synthesis method of phenyl sulfide compound |
| CN104961694A (en) * | 2015-06-23 | 2015-10-07 | 天津师范大学 | Diphenyl sulfide compound displaced with double triazole and preparing method and application thereof |
| CN108997180A (en) * | 2018-09-10 | 2018-12-14 | 浙江扬帆新材料股份有限公司 | A kind of method of one pot process substituted diphenyl sulfide |
| TWI652254B (en) | 2017-08-01 | 2019-03-01 | 財團法人工業技術研究院 | Method for preparing compound and method for preparing polymer employing the same |
| CN109734636A (en) * | 2018-12-29 | 2019-05-10 | 天津久日新材料股份有限公司 | A kind of preparation method of 4- benzoyl -4 '-methyl-diphenyl sulfide |
| US10723841B2 (en) | 2017-08-01 | 2020-07-28 | Industrial Technology Research | Method for preparing compound and method for preparing polymer employing the same |
-
2010
- 2010-01-21 CN CN201010101517A patent/CN101774953A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351622A (en) * | 2011-08-19 | 2012-02-15 | 浙江大学 | Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt |
| CN102351622B (en) * | 2011-08-19 | 2013-12-25 | 浙江大学 | Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt |
| CN102516139A (en) * | 2011-11-02 | 2012-06-27 | 浙江工业大学 | Synthesis method of phenyl sulfide compound |
| CN104961694A (en) * | 2015-06-23 | 2015-10-07 | 天津师范大学 | Diphenyl sulfide compound displaced with double triazole and preparing method and application thereof |
| TWI652254B (en) | 2017-08-01 | 2019-03-01 | 財團法人工業技術研究院 | Method for preparing compound and method for preparing polymer employing the same |
| US10723841B2 (en) | 2017-08-01 | 2020-07-28 | Industrial Technology Research | Method for preparing compound and method for preparing polymer employing the same |
| CN108997180A (en) * | 2018-09-10 | 2018-12-14 | 浙江扬帆新材料股份有限公司 | A kind of method of one pot process substituted diphenyl sulfide |
| CN109734636A (en) * | 2018-12-29 | 2019-05-10 | 天津久日新材料股份有限公司 | A kind of preparation method of 4- benzoyl -4 '-methyl-diphenyl sulfide |
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