CN103113270A - Synthesis method of 4-(3-benzyloxy-phenylsulfanyl)-2-chloro-vinylbenzene - Google Patents
Synthesis method of 4-(3-benzyloxy-phenylsulfanyl)-2-chloro-vinylbenzene Download PDFInfo
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- CN103113270A CN103113270A CN2012104841168A CN201210484116A CN103113270A CN 103113270 A CN103113270 A CN 103113270A CN 2012104841168 A CN2012104841168 A CN 2012104841168A CN 201210484116 A CN201210484116 A CN 201210484116A CN 103113270 A CN103113270 A CN 103113270A
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- phenyl sulfanyl
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- GIQVAHDDKLPDCN-UHFFFAOYSA-N 1-(3-chloro-3-ethenylcyclohexa-1,5-dien-1-yl)sulfanyl-3-phenylmethoxybenzene Chemical compound C(C1=CC=CC=C1)OC=1C=C(C=CC=1)SC1=CC(CC=C1)(C=C)Cl GIQVAHDDKLPDCN-UHFFFAOYSA-N 0.000 title abstract 4
- 238000001308 synthesis method Methods 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 9
- 239000011574 phosphorus Substances 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
- BQSFSNWYCOWKJX-UHFFFAOYSA-N 2-chloro-1-ethenyl-4-(3-phenylmethoxyphenyl)sulfanylbenzene Chemical compound C1=C(C=C)C(Cl)=CC(SC=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 BQSFSNWYCOWKJX-UHFFFAOYSA-N 0.000 claims description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- -1 2-chloro-4 fluorobenzene acetaldehyde Chemical compound 0.000 claims description 16
- VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical compound OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 235000015320 potassium carbonate Nutrition 0.000 claims description 12
- 238000010189 synthetic method Methods 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 9
- 238000010792 warming Methods 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- 238000003032 molecular docking Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- NTKVWOTYTNWGRK-UHFFFAOYSA-N P.Br.Br.Br Chemical compound P.Br.Br.Br NTKVWOTYTNWGRK-UHFFFAOYSA-N 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- VXCOWTCRKHIKCQ-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)acetaldehyde Chemical compound FC1=CC=C(CC=O)C(Cl)=C1 VXCOWTCRKHIKCQ-UHFFFAOYSA-N 0.000 abstract 2
- WZMPOCLULGAHJR-UHFFFAOYSA-N thiophen-2-ol Chemical compound OC1=CC=CS1 WZMPOCLULGAHJR-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 2
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a synthesis method of 4-(3-benzyloxy-phenylsulfanyl)-2-chloro-vinylbenzene. 2-chloro-4-fluorophenylacetaldehyde and 2-thiophenol are used as raw materials, the 2-chloro-4-fluorophenylacetaldehyde and the 2-thiophenol are butt linked by using potassium carbonate, benzylbromide is added to protect a phenolic group, and double bond is generated by means of phosphorus ylide reaction to obtain a target product of the 4-(3-benzyloxy-phenylsulfanyl)-2-chloro-vinylbenzene. By virtue of the method, the synthesis of the 4-(3-benzyloxy-phenylsulfanyl)-2-chloro-vinylbenzene is realized, and the synthesis method is short in path, stable in condition and low in cost.
Description
Technical field
The present invention relates to a kind of 4-(3-benzyloxy-phenyl sulfanyl)-synthesis technology of 2-chloro-1-vinyl benzene improves, and belongs to medicine, chemical technology field.
Background technology
4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene is a kind of white solid, is important medicine intermediate, raw material.
Now find 4-(3-benzyloxy-phenyl sulfanyl)-synthesis technique of 2-chloro-1-vinyl benzene; to adopt take 2-chloro-4 fluorobenzene acetaldehyde and 2-mercapto-phenol as raw material; after upper Bian bromine protection phenolic group after the salt of wormwood docking; generate two keys with the phosphorus ylide reaction, obtain target product 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene.Realized 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene synthetic, and the path is short, and cost is low.
Summary of the invention
For domestic without bibliographical information, the present invention take 2-chloro-4 fluorobenzene acetaldehyde and 2-mercapto-phenol under the prerequisite of raw material, after testing, finally determined the technique circuit of this patent.The trial circuit is, take 2-chloro-4 fluorobenzene acetaldehyde and 2-mercapto-phenol as raw material, after upper Bian bromine protection phenolic group after the salt of wormwood docking, generates two keys with the phosphorus ylide reaction, obtains target product 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene.Adopt this technique, realized 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene synthetic.
The synthetic method of 4-(3-benzyloxy of the present invention-phenyl sulfanyl)-2-chloro-1-vinyl benzene; that after adopting improvement, route reacts; take 2-chloro-4 fluorobenzene acetaldehyde and 2-mercapto-phenol as raw material; after upper Bian bromine protection phenolic group after the salt of wormwood docking; generate two keys with the phosphorus ylide reaction, obtain target product 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene.
The synthetic method of above-mentioned 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene; it is characterized in that: described improvement is take 2-chloro-4 fluorobenzene acetaldehyde and 2-mercapto-phenol as raw material; after upper Bian bromine protection phenolic group after the salt of wormwood docking; generate two keys with the phosphorus ylide reaction, obtain target product 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene.Take this stable route to obtain higher yield.
The synthetic method of above-mentioned 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene is characterized in that: described employing generates two keys with the phosphorus ylide reaction.
The synthetic method of above-mentioned 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene; it is characterized in that: the synthetic method of described 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene makes: add 2-chloro-4 fluorobenzene acetaldehyde (5 gram) in the there-necked flask of 250 ml; salt of wormwood (8.7 gram); methyl-sulphoxide (80 ml) heats up 50 ℃ under nitrogen protection.Then 2-mercapto-phenol (4 gram) is dissolved in 30 ml tetrahydrofuran (THF)s, adds at a slow speed (about 30 minutes) in bottle.Control simultaneously temperature and be no more than 50 ℃.Reaction is 1.5 hours under 50 ℃.Be cooled to 0 ℃.Add 1 N hydrochloric acid.Ethyl acetate extraction, dry filter was spin-dried for post and gets 2-chloro-4-(3-hydroxyl-phenyl sulfanyl)-phenyl aldehyde (6.14 g).Add 2-chloro-4-(3-hydroxyl-phenyl sulfanyl in the there-necked flask of 250 ml)-phenyl aldehyde (6.14 gram); salt of wormwood (7.63 gram); acetonitrile (100 ml); under nitrogen protection; be cooled to 0 ℃. 5.55 gram benzyl bromines are dissolved in the acetonitrile of 30ml; add at a slow speed in bottle (about 30 minutes) to finish, be warming up to 45 ℃ and stirred 1.5 hours.Be cooled to 0 ℃ and add 10% citric acid.Ethyl acetate extraction, drying were spin-dried for post and got 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-aldehyde-base benzene 6.59 grams.Add methyltriphenylphospbromide bromide phosphorus (7.96 gram) in 250 ml there-necked flasks, tetrahydrofuran (THF) (90 ml) is cooled to 0 ℃, adds 2.4 M butyllithiums (9.3 ml) (time was controlled at about 30 minutes). then be warming up to stirring at room 1 hour.Add compound 4(6.59 gram under 0 ℃) solution of 30 ml tetrahydrofuran (THF)s.Then be warming up to stirring at room 3 hours.Add saturated ammonium chloride, ethyl acetate extraction, drying was spin-dried for post, got 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene (5.48 gram).
Above-mentioned with 2-chloro-4 fluorobenzene acetaldehyde, 2-mercapto-phenol, Bian bromine and methyltriphenylphospbromide bromide phosphorus etc. are the synthetic 4-(3-benzyloxy of raw material-phenyl sulfanyl)-chemical reaction and the reaction formula of 2-chloro-1-vinyl benzene is as follows:
(1) reaction equation of 2-chloro-4 fluorobenzene acetaldehyde and 2-mercapto-phenol is:
(2) reaction is completed, after purifying and the reaction equation of Bian bromine be:
(3) reaction is completed, and after purifying with the reaction equation of methyl triphenyl bromine phosphine is again:
Embodiment
Embodiment:
The synthetic method of described 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene makes: add 2-chloro-4 fluorobenzene acetaldehyde (5 gram) in the there-necked flask of 250 ml; salt of wormwood (8.7 gram); methyl-sulphoxide (80 ml) heats up 50 ℃ under nitrogen protection.Then 2-mercapto-phenol (4 gram) is dissolved in 30 ml tetrahydrofuran (THF)s, adds at a slow speed (about 30 minutes) in bottle.Control simultaneously temperature and be no more than 50 ℃.Reaction is 1.5 hours under 50 ℃.Be cooled to 0 ℃.Add 1 N hydrochloric acid.Ethyl acetate extraction, dry filter was spin-dried for post and gets 2-chloro-4-(3-hydroxyl-phenyl sulfanyl)-phenyl aldehyde (6.14 gram).Add 2-chloro-4-(3-hydroxyl-phenyl sulfanyl in the there-necked flask of 250 ml)-phenyl aldehyde (6.14 gram); salt of wormwood (7.63 gram); acetonitrile (100 ml); under nitrogen protection; be cooled to 0 ℃. 5.55 gram benzyl bromines are dissolved in the acetonitrile of 30ml; add at a slow speed in bottle (about 30 minutes) to finish, be warming up to 45 ℃ and stirred 1.5 hours.Be cooled to 0 ℃ and add 10% citric acid.Ethyl acetate extraction, drying were spin-dried for post and got 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-aldehyde-base benzene 6.59 grams.Add methyltriphenylphospbromide bromide phosphorus (7.96 gram) in 250 ml there-necked flasks, tetrahydrofuran (THF) (90 ml) is cooled to 0 ℃, adds 2.4 M butyllithiums (9.3 ml) (time was controlled at about 30 minutes). then be warming up to stirring at room 1 hour.Add compound 4(6.59 gram under 0 ℃) solution of 30 ml tetrahydrofuran (THF)s.Then be warming up to stirring at room 3 hours.Add saturated ammonium chloride, ethyl acetate extraction, drying was spin-dried for post, got 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene (5.48 gram).
Claims (4)
1.4-(3-the synthetic method of benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene; that after adopting improvement, route reacts; take 2-chloro-4 fluorobenzene acetaldehyde and 2-mercapto-phenol as raw material; after upper Bian bromine protection phenolic group after the salt of wormwood docking; generate two keys with the phosphorus ylide reaction, obtain target product 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene.
2. the synthetic method of 4-(3-benzyloxy-phenyl sulfanyl as claimed in claim)-2-chloro-1-vinyl benzene; it is characterized in that: described improvement is take 2-chloro-4 fluorobenzene acetaldehyde and 2-mercapto-phenol as raw material; after upper Bian bromine protection phenolic group after the salt of wormwood docking; generate two keys with the phosphorus ylide reaction; obtain target product 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene, route after this improvement.
3. the synthetic method of 4-(3-benzyloxy-phenyl sulfanyl as claimed in claim)-2-chloro-1-vinyl benzene, it is characterized in that: described employing generates two keys with the phosphorus ylide reaction.
4. the synthetic method of 4-(3-benzyloxy-phenyl sulfanyl as claimed in claim)-2-chloro-1-vinyl benzene, it is characterized in that: the synthetic method of described 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene makes: add 2-chloro-4 fluorobenzene acetaldehyde (5 gram) in the there-necked flask of 250 ml, salt of wormwood (8.7 gram), methyl-sulphoxide (80 ml), heat up 50 ℃ under nitrogen protection, then 2-mercapto-phenol (4 gram) is dissolved in 30 ml tetrahydrofuran (THF)s, add at a slow speed (about 30 minutes) in bottle, control simultaneously temperature and be no more than 50 ℃, reaction is 1.5 hours under 50 ℃, be cooled to 0 ℃, add 1 N hydrochloric acid, ethyl acetate extraction, dry filter, be spin-dried for post and got 2-chloro-4-(3-hydroxyl-phenyl sulfanyl)-phenyl aldehyde (6.14 g), add 2-chloro-4-(3-hydroxyl-phenyl sulfanyl in the there-necked flask of 250 ml)-phenyl aldehyde (6.14 gram), salt of wormwood (7.63 gram), acetonitrile (100 ml), under nitrogen protection, be cooled to 0 ℃. 5.55 gram benzyl bromines are dissolved in the acetonitrile of 30ml, add at a slow speed in bottle (about 30 minutes) to finish, being warming up to 45 ℃ stirred 1.5 hours, be cooled to 0 ℃ and add 10% citric acid, ethyl acetate extraction, drying was spin-dried for post and got 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-aldehyde-base benzene 6.59 grams, add methyltriphenylphospbromide bromide phosphorus (7.96 gram) in 250 ml there-necked flasks, tetrahydrofuran (THF) (90 ml), be cooled to 0 ℃, add 2.4 M butyllithiums (9.3 ml) (time was controlled at about 30 minutes). then be warming up to stirring at room 1 hour, add compound 4(6.59 gram under 0 ℃) solution of 30 ml tetrahydrofuran (THF)s, then be warming up to stirring at room 3 hours, add saturated ammonium chloride, ethyl acetate extraction, drying was spin-dried for post, get 4-(3-benzyloxy-phenyl sulfanyl)-2-chloro-1-vinyl benzene (5.48 gram).
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012104841168A CN103113270A (en) | 2012-11-26 | 2012-11-26 | Synthesis method of 4-(3-benzyloxy-phenylsulfanyl)-2-chloro-vinylbenzene |
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| CN2012104841168A CN103113270A (en) | 2012-11-26 | 2012-11-26 | Synthesis method of 4-(3-benzyloxy-phenylsulfanyl)-2-chloro-vinylbenzene |
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| CN2012104841168A Pending CN103113270A (en) | 2012-11-26 | 2012-11-26 | Synthesis method of 4-(3-benzyloxy-phenylsulfanyl)-2-chloro-vinylbenzene |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003029205A1 (en) * | 2001-09-27 | 2003-04-10 | Kyorin Pharmaceutical Co., Ltd. | Diaryl sulfide derivative, addition salt thereof, and immunosuppressant |
| WO2006041019A1 (en) * | 2004-10-12 | 2006-04-20 | Kyorin Pharmaceutical Co., Ltd. | Process for producing 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride or hydrate thereof and intermediate for the same |
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2012
- 2012-11-26 CN CN2012104841168A patent/CN103113270A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003029205A1 (en) * | 2001-09-27 | 2003-04-10 | Kyorin Pharmaceutical Co., Ltd. | Diaryl sulfide derivative, addition salt thereof, and immunosuppressant |
| WO2006041019A1 (en) * | 2004-10-12 | 2006-04-20 | Kyorin Pharmaceutical Co., Ltd. | Process for producing 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride or hydrate thereof and intermediate for the same |
Non-Patent Citations (1)
| Title |
|---|
| MASAO CHINO 等: "An efficient total synthsis of a sphingosine-1-phosphate receptor agonist KRP-203", 《TETRAHEDRON》 * |
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