CN1535959A - Chemical synthesis method of 3-phenyl-5-methylisoxazole-4-formyl chloride - Google Patents
Chemical synthesis method of 3-phenyl-5-methylisoxazole-4-formyl chloride Download PDFInfo
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- CN1535959A CN1535959A CNA031162207A CN03116220A CN1535959A CN 1535959 A CN1535959 A CN 1535959A CN A031162207 A CNA031162207 A CN A031162207A CN 03116220 A CN03116220 A CN 03116220A CN 1535959 A CN1535959 A CN 1535959A
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- Prior art keywords
- phenyl
- methyl
- isoxzzole
- formic acid
- trichloromethyl
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Links
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title abstract description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 61
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 30
- 235000019253 formic acid Nutrition 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- SNDGLCYYBKJSOT-UHFFFAOYSA-N 1,1,3,3-tetrabutylurea Chemical compound CCCCN(CCCC)C(=O)N(CCCC)CCCC SNDGLCYYBKJSOT-UHFFFAOYSA-N 0.000 claims description 10
- 150000002170 ethers Chemical class 0.000 claims description 10
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 abstract description 4
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 abstract 1
- 229960001019 oxacillin Drugs 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 14
- 238000009835 boiling Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 150000008422 chlorobenzenes Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- -1 5-Methyl-3-phenyl-isoxazole 5-Methyl-3-phenyl-isoxazole Chemical compound 0.000 description 1
- HXEVQMXCHCDPSO-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride Chemical compound ClC(=O)C1=C(C)ON=C1C1=CC=CC=C1 HXEVQMXCHCDPSO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- VDUVBBMAXXHEQP-SLINCCQESA-M oxacillin sodium Chemical compound [Na+].N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C([O-])=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 VDUVBBMAXXHEQP-SLINCCQESA-M 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The present invention relates to a chemical synthesis method of 3-phenyl-5-methyl-4-isoxazole formyl chloride. It is made up by using bis (trichloromethyl) carbonate and 3-phenyl-5-methyl-4-isoxazole formic acid as raw material and making them undergo the acyl-chlorination reaction in organic solvent. The product is a key intermediate body of oxazocilline, and said synthesis method is reasonable in technological process, high in reaction yield and low in production cost.
Description
Technical field
The present invention relates to the chemical synthesis process that two (trichloromethyl) carbonic ethers [bis (trichloromethyl) carbonate] of a kind of usefulness substitute sulfur oxychloride or phosphorus oxychloride or phosphorus pentachloride or phosphorus trichloride and 3-phenyl-5-methyl isoxzzole-4-formic acid prepared in reaction 3-phenyl-5-methyl isoxzzole-4-formyl chloride (3-phenyl-5-Methylisoxazole-4-carbonylChloride), 3-phenyl-5-methyl isoxzzole-4-formyl chloride is the key intermediate of Prostaphlin.
Background technology
Before the present invention made, the chemical synthesis process of prior art 3-phenyl-5-methyl 4-isoxzzole formyl chloride was to be that raw material reaction makes with sulfur oxychloride or phosphorus oxychloride or phosphorus pentachloride or phosphorus trichloride and 3-phenyl-5-methyl 4-isoxzzole formic acid.Propose as US 2996501 (1961), react with 0.1 mole 3-phenyl-5-methyl-4-isoxzzole formic acid and 0.48 mole sulfur oxychloride and synthesize 3-phenyl-5-methyl-4-isoxzzole formyl chloride.The shortcoming of this technology be use in the world that control uses than toxogen material sulfur oxychloride, equipment corrosion is serious, trouble is that quantity of three wastes is big, and difficult treatment, expense height.
Summary of the invention
Task of the present invention is the shortcoming that overcomes prior art, provides that a kind of technology is reasonable, production safety is reliable, reaction yield is high, production cost is low, does not have the 3-phenyl-5-methyl 4-isoxzzole formyl chloride chemical synthesis process of the three wastes substantially.
The chemical synthesis process of 3-phenyl-5-methyl isoxzzole-4-formyl chloride, it is characterized in that in organic solvent with two (trichloromethyl) carbonic ethers directly and 3-phenyl-5-methyl-4-isoxzzole formic acid make through acyl chloride reaction, its molar ratio is 3-phenyl-5-methyl-4-isoxzzole formic acid: two (trichloromethyl) carbonic ether: catalyzer=1: 0.34～1: 0.001～0.1, consumption of organic solvent is 5-15 a times of 3-(2-chloro-phenyl-)-5-methyl-4-isoxzzole formic acid quality, its temperature of reaction is 20～150 ℃, reaction times is 1～6 hour, and its reaction equation is:
5-Methyl-3-phenyl-isoxazole 5-Methyl-3-phenyl-isoxazole
-4-carboxylic?acid -4-carbonyl?chloride
Organic solvent can be benzene or toluene or dimethylbenzene or chlorobenzene or dichlorobenzene or tetrahydrofuran (THF) or methylene dichloride or trichloromethane or tetracol phenixin or ethylene dichloride.
Catalyzer can be tetrabutyl urea or triethylamine or pyridine or 3-picoline or N-methylpyrrole or N-methyl Pyrrolidine or N, dinethylformamide.
The present invention compared with prior art, the operational path advanced person, processing condition are reasonable, used raw material avoided that control in the world uses than toxogen material sulfur oxychloride or phosphorus oxychloride or phosphorus pentachloride or phosphorus trichloride, production safety is reliable, the reaction yield height, generally more than 95%, production cost is lower, and equipment corrosion is little, few and the easy processing of the three wastes has bigger implementary value and economic results in society.
Embodiment
Embodiment 1
3-phenyl-5-methyl-4-isoxzzole formic acid: two (trichloromethyl) carbonic ether: N, dinethylformamide=1: 0.34: 0.01 (mol ratio), chlorobenzene consumption are 8 times of 3-(2-chloro-phenyl-)-5-methyl-4-isoxzzole formic acid quality.
In thermometer, reflux condensing tube and churned mechanically 500 milliliters of four-hole boiling flasks are housed, add 100 milliliters of chlorobenzenes, 22 gram 99.2%3-phenyl-5-methyl-4-isoxzzole formic acid, open and stir, add N in proportion, the chlorobenzene solution of dinethylformamide and two (trichloromethyl) carbonic ethers.Be warming up to 130 ℃ under stirring, held stationary back flow reaction 2 hours, reaction finishes the back underpressure distillation and reclaims chlorobenzene, the last cut of collecting 153-155 ℃ under 0.667KPa.Yield is 93.6%.Through the high-performance liquid chromatogram determination product purity is 99.5%.
Embodiment 2
3-phenyl-5-methyl-4-isoxzzole formic acid: two (trichloromethyl) carbonic ether: N, dinethylformamide=1: 0.34: 0.005 (mol ratio), chlorobenzene consumption are 8 times of 3-(2-chloro-phenyl-)-5-methyl-4-isoxzzole formic acid quality.
In thermometer, reflux condensing tube and churned mechanically 500 milliliters of four-hole boiling flasks are housed, add 100 milliliters and reclaim chlorobenzene, 22 gram 99.2%3-phenyl-5-methyl-4-isoxzzole formic acid, open and stir, add N in proportion, the chlorobenzene solution of dinethylformamide and two (trichloromethyl) carbonic ethers.Be warming up to 130 ℃ under stirring, held stationary back flow reaction 5 hours, reaction finishes the back underpressure distillation and reclaims chlorobenzene, the last cut of collecting 153-155 ℃ under 0.667KPa.Yield is 95.1%.Through the high-performance liquid chromatogram determination product purity is 99.8%.
Embodiment 3
3-phenyl-5-methyl-4-isoxzzole formic acid: two (trichloromethyl) carbonic ether: N, dinethylformamide=1: 0.5: 0.01 (mol ratio), chlorobenzene consumption are 8 times of 3-(2-chloro-phenyl-)-5-methyl-4-isoxzzole formic acid quality.
In thermometer, reflux condensing tube and churned mechanically 500 milliliters of four-hole boiling flasks are housed, add 100 milliliters of chlorobenzenes, 22 gram content are 3-phenyl-5-methyl-4-isoxzzole formic acid of 99.2%, open and stir, add N in proportion, behind the dinethylformamide, drip the chlorobenzene solution of two (trichloromethyl) carbonic ethers at room temperature 30 minutes.Be warming up to 130 ℃ under stirring, held stationary back flow reaction 3 hours, reaction finishes the back underpressure distillation and reclaims chlorobenzene, the last cut of collecting 153-155 ℃ under 0.667KPa.Yield is 96.0%.Through the high-performance liquid chromatogram determination product purity is 99.5%.
Embodiment 4
3-phenyl-5-methyl-4-isoxzzole formic acid: two (trichloromethyl) carbonic ether: tetrabutyl urea=1: 0.50: 0.05 (mol ratio), toluene consumption are 12 times of 3-(2-chloro-phenyl-)-5-methyl-4-isoxzzole formic acid quality.
In thermometer, reflux condensing tube and churned mechanically 500 milliliters of four-hole boiling flasks are housed, add 100 milliliters of toluene, 22 gram 99.2%3-phenyl-5-methyl-4-isoxzzole formic acid, open and stir, add the toluene solution of tetrabutyl urea and two (trichloromethyl) carbonic ethers in proportion.Be warming up to 110 ℃ under stirring, held stationary back flow reaction 3 hours, reaction finishes the back underpressure distillation and reclaims toluene, the last cut of collecting 153-155 ℃ under 0.667KPa.Yield is 96.2%.Through the high-performance liquid chromatogram determination product purity is 99.7%.
Embodiment 5
3-phenyl-5-methyl-4-isoxzzole formic acid: two (trichloromethyl) carbonic ether: tetrabutyl urea=1: 0.50: 0.02 (mol ratio), recovery toluene consumption are 10 times of 3-(2-chloro-phenyl-)-5-methyl-4-isoxzzole formic acid quality.
In thermometer, reflux condensing tube and churned mechanically 500 milliliters of four-hole boiling flasks are housed, add 100 milliliters and reclaim toluene, 22 gram 99.2%3-phenyl-5-methyl-4-isoxzzole formic acid, open and stir, add the toluene solution of tetrabutyl urea and two (trichloromethyl) carbonic ethers in proportion.Be warming up to 110 ℃ under stirring, held stationary back flow reaction 5 hours, reaction finishes the back underpressure distillation and reclaims toluene, the last cut of collecting 153-155 ℃ under 0.667KPa.Yield is 97.3%.Through the high-performance liquid chromatogram determination product purity is 99.8%.
Embodiment 6
3-phenyl-5-methyl-4-isoxzzole formic acid: two (trichloromethyl) carbonic ether: tetrabutyl urea=1: 0.50: 0.02 (mol ratio), benzene consumption are 12 times of 3-(2-chloro-phenyl-)-5-methyl-4-isoxzzole formic acid quality.
In thermometer, reflux condensing tube and churned mechanically 500 milliliters of four-hole boiling flasks are housed, add 100 milliliters of benzene, 22 gram 99.2%3-phenyl-5-methyl-4-isoxzzole formic acid, open and stir, add the toluene solution of tetrabutyl urea and two (trichloromethyl) carbonic ethers in proportion.Be warming up to 80 ℃ under stirring, held stationary back flow reaction 6 hours, reaction finishes the back underpressure distillation and reclaims benzene, the last cut of collecting 153-155 ℃ under 0.667KPa.Yield is 95.8%.Through the high-performance liquid chromatogram determination product purity is 99.6%.
Embodiment 7
3-phenyl-5-methyl-4-isoxzzole formic acid: two (trichloromethyl) carbonic ether: tetrabutyl urea=1: 0.50: 0.02 (mol ratio), tetrahydrofuran (THF) consumption are 10 times of 3-(2-chloro-phenyl-)-5-methyl-4-isoxzzole formic acid quality.
In thermometer, reflux condensing tube and churned mechanically 500 milliliters of four-hole boiling flasks are housed, add 100 milliliters and reclaim tetrahydrofuran (THF), 22 gram 99.2%3-phenyl-5-methyl-4-isoxzzole formic acid, open and stir, add the tetrahydrofuran solution of tetrabutyl urea and two (trichloromethyl) carbonic ethers in proportion.Be warming up to 30 ℃ under stirring, held stationary back flow reaction 8 hours, reaction finishes the back underpressure distillation and reclaims tetrahydrofuran (THF), the last cut of collecting 153-155 ℃ under 0.667KPa.Yield is 95.0%.Through the high-performance liquid chromatogram determination product purity is 99.1%.
The present invention compares with existing technology, has production safety, and equipment corrosion is little, and is easy to operate, and reaction is received The rate height, the few and easy processing of the three wastes, the advantages such as good product quality are methods that is suitable for suitability for industrialized production.
Claims (3)
1, the chemical synthesis process of 3-phenyl-5-methyl isoxzzole-4-formyl chloride, it is characterized in that with two (trichloromethyl) carbonic ethers and 3-phenyl-5-methyl-4-isoxzzole formic acid being to react under the effect of raw material catalyzer in organic solvent to make, its molar ratio is 3-phenyl-5-methyl-4-isoxzzole formic acid: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.34～0.8: 0.001-0.1; Its consumption of organic solvent is 3-15 a times of 3-phenyl-5-methyl-4-isoxzzole formic acid quality; Its temperature of reaction is 20-150 ℃; Its reaction times is 1～10 hour.
2,, it is characterized in that organic solvent can be tetrahydrofuran (THF) or ethyl acetate or benzene or toluene or dimethylbenzene or chlorobenzene or orthodichlorobenzene or Meta Dichlorobenzene or santochlor or trichloromethane or tetracol phenixin or ethylene dichloride as the said chemical synthesis process of claim 1.
3,, it is characterized in that catalyzer can be triethylamine or pyridine or 3-picoline or N-methylpyrrole or N-methyl Pyrrolidine or N, dinethylformamide or tetrabutyl urea as the said chemical synthesis process of claim 1.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03116220 CN1233634C (en) | 2003-04-03 | 2003-04-03 | Chemical synthesis method of 3-phenyl-5-methylisoxazole-4-formyl chloride |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03116220 CN1233634C (en) | 2003-04-03 | 2003-04-03 | Chemical synthesis method of 3-phenyl-5-methylisoxazole-4-formyl chloride |
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| Publication Number | Publication Date |
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| CN1535959A true CN1535959A (en) | 2004-10-13 |
| CN1233634C CN1233634C (en) | 2005-12-28 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100467455C (en) * | 2007-02-14 | 2009-03-11 | 浙江工业大学 | Synthetic method for 3-(2'-chloro-6'-fluorophenyl)-5-methyl-4-isooxazole formyl chloride |
| CN100537510C (en) * | 2006-08-04 | 2009-09-09 | 浙江工业大学 | Chemical method for synthesizing palmitoyl chloride |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100500633C (en) * | 2006-09-29 | 2009-06-17 | 浙江工业大学 | Acetoxy acetyl chloride chemical synthesizing method |
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2003
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100537510C (en) * | 2006-08-04 | 2009-09-09 | 浙江工业大学 | Chemical method for synthesizing palmitoyl chloride |
| CN100467455C (en) * | 2007-02-14 | 2009-03-11 | 浙江工业大学 | Synthetic method for 3-(2'-chloro-6'-fluorophenyl)-5-methyl-4-isooxazole formyl chloride |
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| Publication number | Publication date |
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| CN1233634C (en) | 2005-12-28 |
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