CN1456549A - 2-[2'-fluorosulphuric radical] teredimethyl ether and its synthesis and uses - Google Patents
2-[2'-fluorosulphuric radical] teredimethyl ether and its synthesis and uses Download PDFInfo
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- CN1456549A CN1456549A CN 03128051 CN03128051A CN1456549A CN 1456549 A CN1456549 A CN 1456549A CN 03128051 CN03128051 CN 03128051 CN 03128051 A CN03128051 A CN 03128051A CN 1456549 A CN1456549 A CN 1456549A
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- ether
- terephthaldehyde
- ethylmercapto group
- fluorine ethylmercapto
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Abstract
A compound 2-[2'-fluoroethylthio] p-phenyldimethyl ether is prepared from 2.5-dimethoxy phenylsulfonyl chloride through reducing at 70-80 deg.C by zinc powder in acidic condition, vacuum distilling to obtain 2-mercapto p-phenyldimethyl ether, condensing with 1-fluoro-2-bromoethane at 60-80 deg.C in alkaline condition, diluting in water, extracting with dichloromethane, and vacuum distilling. It can be used to synthesize 2.5-dimethoxy-4-[2'-fluoroethylthio] benzaldehyde.
Description
Technical field
The present invention relates to 2-[2 '-fluorine ethylmercapto group] terephthaldehyde's ether and preparation method and use thereof.
Background technology
As a kind of new compound, 2-[2 '-fluorine ethylmercapto group] terephthaldehyde's ether and synthetic method thereof do not see bibliographical information as yet.
Summary of the invention
Task of the present invention provides a kind of new compound 2-[2 '-fluorine ethylmercapto group] terephthaldehyde's ether and preparation method and use thereof.
Technical scheme provided by the invention is: 2-[2 '-fluorine ethylmercapto group] terephthaldehyde's ether, its structural formula is
The present invention also provides the synthetic method of above-claimed cpd, and with 2,5-dimethoxy benzene sulfonyl chloride is a raw material, under 70～80 ℃, acidic conditions (pH＜1), uses zinc powder reduction, and underpressure distillation then obtains 2-sulfydryl terephthaldehyde ether; Gained 2-sulfydryl terephthaldehyde ether is required 2-[2 '-fluorine ethylmercapto group through the colourless transparent liquid that water is released, dichloromethane extraction, underpressure distillation obtain at 60～80 ℃, alkaline condition (pH＞10) down and the condensation of 1-fluoro-2-monobromethane then] terephthaldehyde's ether.
Above-mentioned 2,5-dimethoxy benzene sulfonyl chloride can prepare by following method: ethylene dichloride and terephthaldehyde's ether are mixed stirring and dissolving, be cooled to 0～10 ℃ of following agitation and dropping chlorsulfonic acid and sulfur oxychloride, tell lower floor's oil reservoir, to its distill yellow solid 2,5-dimethoxy benzene sulfonyl chloride.
The reaction equation of said process is as follows:
The 2-[2 '-fluorine ethylmercapto group of the present invention preparation] terephthaldehyde's ether can be used for Synthetic 2,5-dimethoxy-4 '-[2 '-fluorine ethylmercapto group]-phenyl aldehyde.
Embodiment
In the 250ml there-necked flask, add 105ml ethylene dichloride, 13.5g terephthaldehyde ether, stirring and dissolving, ice bath cooling (0～10 ℃), stir and drip 26.5ml chlorsulfonic acid and 10ml sulfur oxychloride down, reacted 2 hours, and with in its impouring 280ml frozen water, told lower floor's oil reservoir under stirring, steam and remove methylene dichloride (recovery), get yellow solid 2,5-dimethoxy benzene sulfonyl chloride, oven-dried weight 19.8g, productive rate 85%, fusing point 115-117 ℃.
In the 500ml there-necked flask, add the 68ml water and the 23ml vitriol oil, when treating that temperature drops to about 70 ℃, adding 12g 2,5-dimethoxy benzene sulfonyl chloride and 18g zinc powder reacted 1 hour down at 80 ℃, and filtration, decompression, steaming are slipped and are obtained 8.2g 2-sulfydryl terephthaldehyde ether.
In the 250ml there-necked flask, add 100ml methyl alcohol, 6.9 gram potassium hydroxide is preheating to 50～60 ℃, add 13.0g 2-sulfydryl terephthaldehyde's ether and 9.6g1-fluoro-2-monobromethane successively, reflux (about 70 ℃) 2 hours, then reaction solution is under agitation poured in the 1000ml water, with 100ml dichloromethane extraction three times, extraction liquid merges, with the sodium hydroxide washing of 5% (weight percent), after steaming desolventizes, underpressure distillation, collect the cut of 150 ℃/2mmHg, get colourless transparent liquid 2-[2 '-fluorine ethylmercapto group] terephthaldehyde's ether 16.0g, productive rate 97%, analyze content 〉=98% through HPLC.
2 of the present invention's preparation, 5-dimethoxy ethyl phenyl sulfide can be used for Synthetic 2,5-dimethoxy-4 '-[2 '-fluorine ethylmercapto group]-phenyl aldehyde: toward 13.4 gram N, add 26.8 gram phosphorus oxychloride in the dinethylformamide, heated ten minutes down, add 16.8 gram 2-[2 '-fluorine ethylmercapto groups again at 60 ℃] terephthaldehyde's ether, 70 ℃ of stirring reactions 1 hour, reaction solution poured in 1.5 liters 55 ℃ the warm water, 15.1 gram yellow solids 2,5-dimethoxy-4 '-[2 '-fluorine ethylmercapto group]-phenyl aldehyde.
Claims (4)
1. 2-[2 '-fluorine ethylmercapto group] terephthaldehyde's ether, its structural formula is:
2. 2-[2 '-fluorine ethylmercapto group] synthetic method of terephthaldehyde's ether, it is characterized in that: with 2,5-dimethoxy benzene sulfonyl chloride is a raw material, under 70～80 ℃, acidic conditions, uses zinc powder reduction, underpressure distillation then obtains 2-sulfydryl terephthaldehyde ether; Gained 2-sulfydryl terephthaldehyde ether in 60～80 ℃, the methanol solution of alkalescence with the condensation of 1-fluoro-2-monobromethane, through required 2-[2 '-fluorine ethylmercapto group that water is released, dichloromethane extraction, underpressure distillation obtain] terephthaldehyde's ether.
3. synthetic method according to claim 2, it is characterized in that: 2,5-dimethoxy benzene sulfonyl chloride makes by following method, ethylene dichloride and terephthaldehyde's ether are mixed stirring and dissolving, be cooled to 0～10 ℃ of following agitation and dropping chlorsulfonic acid and sulfur oxychloride, tell lower floor's oil reservoir, to its distill 2,5-dimethoxy benzene sulfonyl chloride.
4. 2-[2 '-fluorine ethylmercapto group] terephthaldehyde's ether is used for Synthetic 2,5-dimethoxy-4 '-[2 '-fluorine ethylmercapto group]-phenyl aldehyde.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03128051 CN1228321C (en) | 2003-05-28 | 2003-05-28 | 2-[2'-fluorosulphuric radical] teredimethyl ether and its synthesis and uses |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03128051 CN1228321C (en) | 2003-05-28 | 2003-05-28 | 2-[2'-fluorosulphuric radical] teredimethyl ether and its synthesis and uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1456549A true CN1456549A (en) | 2003-11-19 |
| CN1228321C CN1228321C (en) | 2005-11-23 |
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| CN 03128051 Expired - Fee Related CN1228321C (en) | 2003-05-28 | 2003-05-28 | 2-[2'-fluorosulphuric radical] teredimethyl ether and its synthesis and uses |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013157229A1 (en) * | 2012-04-20 | 2013-10-24 | クミアイ化学工業株式会社 | Alkylphenylsulphide derivative and pest control agent |
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2003
- 2003-05-28 CN CN 03128051 patent/CN1228321C/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013157229A1 (en) * | 2012-04-20 | 2013-10-24 | クミアイ化学工業株式会社 | Alkylphenylsulphide derivative and pest control agent |
| KR20150013487A (en) * | 2012-04-20 | 2015-02-05 | 구미아이 가가쿠 고교 가부시키가이샤 | Alkylphenylsulphide derivative and pest control agent |
| CN104350039A (en) * | 2012-04-20 | 2015-02-11 | 组合化学工业株式会社 | Alkylphenylsulphide derivative and pest control agent |
| JPWO2013157229A1 (en) * | 2012-04-20 | 2015-12-21 | クミアイ化学工業株式会社 | Alkylphenyl sulfide derivatives and pest control agents |
| US9332754B2 (en) | 2012-04-20 | 2016-05-10 | Kumiai Chemical Industry Co., Ltd. | Alkyl phenyl sulfide derivative and pest control agent |
| AU2013250690B2 (en) * | 2012-04-20 | 2017-01-19 | Ihara Chemical Industry Co., Ltd. | Alkylphenylsulphide derivative and pest control agent |
| TWI606032B (en) * | 2012-04-20 | 2017-11-21 | 組合化學工業股份有限公司 | Alkyl phenyl sulfide derivatives and pest control agents |
| US10023532B2 (en) | 2012-04-20 | 2018-07-17 | Kumiai Chemical Industry Co., Ltd. | Alkyl phenyl sulfide derivative and pest control agent |
| KR102046801B1 (en) * | 2012-04-20 | 2019-11-20 | 구미아이 가가쿠 고교 가부시키가이샤 | Alkylphenylsulphide derivative and pest control agent |
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| Publication number | Publication date |
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| CN1228321C (en) | 2005-11-23 |
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