SU603339A3 - Способ получени бромпроизводных фурана или тиофена - Google Patents
Способ получени бромпроизводных фурана или тиофенаInfo
- Publication number
- SU603339A3 SU603339A3 SU752111077A SU2111077A SU603339A3 SU 603339 A3 SU603339 A3 SU 603339A3 SU 752111077 A SU752111077 A SU 752111077A SU 2111077 A SU2111077 A SU 2111077A SU 603339 A3 SU603339 A3 SU 603339A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- bromine
- thiophene
- bromo
- solution
- reaction
- Prior art date
Links
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 title description 47
- 238000000034 method Methods 0.000 title description 18
- 229930192474 thiophene Natural products 0.000 title description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 44
- 229910052794 bromium Inorganic materials 0.000 description 44
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 20
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000005286 illumination Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- -1 thiophene bromo derivatives Chemical class 0.000 description 10
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 10
- 229910052721 tungsten Inorganic materials 0.000 description 10
- 239000010937 tungsten Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 150000003577 thiophenes Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- KQFADYXPELMVHE-UHFFFAOYSA-N 2-chloro-3-methylthiophene Chemical compound CC=1C=CSC=1Cl KQFADYXPELMVHE-UHFFFAOYSA-N 0.000 description 2
- UFRQDLJDTSUKCS-UHFFFAOYSA-N 2-chlorothiophene-3-carbaldehyde Chemical compound ClC=1SC=CC=1C=O UFRQDLJDTSUKCS-UHFFFAOYSA-N 0.000 description 2
- SLDBAXYJAIRQMX-UHFFFAOYSA-N 3-ethylthiophene Chemical compound CCC=1C=CSC=1 SLDBAXYJAIRQMX-UHFFFAOYSA-N 0.000 description 2
- SEBRPHZZSLCDRQ-UHFFFAOYSA-N 3-methyl-1-benzothiophene Chemical class C1=CC=C2C(C)=CSC2=C1 SEBRPHZZSLCDRQ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 206010062717 Increased upper airway secretion Diseases 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 208000026435 phlegm Diseases 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000001429 visible spectrum Methods 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- NXSVNPSWARVMAY-UHFFFAOYSA-N 1-benzothiophene-2-carbaldehyde Chemical compound C1=CC=C2SC(C=O)=CC2=C1 NXSVNPSWARVMAY-UHFFFAOYSA-N 0.000 description 1
- BVGDXDCULRNXRH-UHFFFAOYSA-N 2,5-bis(bromomethyl)furan Chemical compound BrCC1=CC=C(CBr)O1 BVGDXDCULRNXRH-UHFFFAOYSA-N 0.000 description 1
- PZYXTWFXPPWJJK-UHFFFAOYSA-N 2,5-dibromo-3-(dibromomethyl)thiophene Chemical compound BrC(Br)C=1C=C(Br)SC=1Br PZYXTWFXPPWJJK-UHFFFAOYSA-N 0.000 description 1
- BUWSFDLUTRHPBO-UHFFFAOYSA-N 2,5-dichloro-3-methylthiophene Chemical compound CC=1C=C(Cl)SC=1Cl BUWSFDLUTRHPBO-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- HGPATVJUCMLGIY-UHFFFAOYSA-N 2-(bromomethyl)-1-benzothiophene Chemical compound C1=CC=C2SC(CBr)=CC2=C1 HGPATVJUCMLGIY-UHFFFAOYSA-N 0.000 description 1
- CBIRJGAGQHWIPM-UHFFFAOYSA-N 2-(bromomethyl)-5-methylfuran Chemical compound CC1=CC=C(CBr)O1 CBIRJGAGQHWIPM-UHFFFAOYSA-N 0.000 description 1
- YYJBWYBULYUKMR-UHFFFAOYSA-N 2-bromo-3-methylthiophene Chemical compound CC=1C=CSC=1Br YYJBWYBULYUKMR-UHFFFAOYSA-N 0.000 description 1
- XXTBLEISCRHFLM-UHFFFAOYSA-N 3-(1-bromoethyl)thiophene Chemical compound CC(Br)C=1C=CSC=1 XXTBLEISCRHFLM-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- GQUZXULTSUGIRF-UHFFFAOYSA-N 3-bromo-1-benzothiophene-2-carbaldehyde Chemical compound C1=CC=C2C(Br)=C(C=O)SC2=C1 GQUZXULTSUGIRF-UHFFFAOYSA-N 0.000 description 1
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
- COWZPSUDTMGBAT-UHFFFAOYSA-N 5-bromothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)S1 COWZPSUDTMGBAT-UHFFFAOYSA-N 0.000 description 1
- VFEAMMGYJFFXKV-UHFFFAOYSA-N 5-formylthiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(C=O)S1 VFEAMMGYJFFXKV-UHFFFAOYSA-N 0.000 description 1
- VCNGNQLPFHVODE-UHFFFAOYSA-N 5-methylthiophene-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)S1 VCNGNQLPFHVODE-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001602876 Nata Species 0.000 description 1
- 208000032820 Ring chromosome 13 syndrome Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000655 anti-hydrolysis Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical compound [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9116/74A GB1483349A (en) | 1974-02-28 | 1974-02-28 | Halogenation of heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU603339A3 true SU603339A3 (ru) | 1978-04-15 |
Family
ID=9865678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752111077A SU603339A3 (ru) | 1974-02-28 | 1975-02-27 | Способ получени бромпроизводных фурана или тиофена |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3947336A (en, 2012) |
| JP (1) | JPS50123657A (en, 2012) |
| BE (1) | BE825833A (en, 2012) |
| CA (1) | CA1036099A (en, 2012) |
| CH (1) | CH597213A5 (en, 2012) |
| DE (1) | DE2508335A1 (en, 2012) |
| ES (1) | ES435064A1 (en, 2012) |
| FR (1) | FR2262651B1 (en, 2012) |
| GB (1) | GB1483349A (en, 2012) |
| HU (1) | HU173013B (en, 2012) |
| IE (1) | IE41774B1 (en, 2012) |
| IT (1) | IT1029881B (en, 2012) |
| NL (1) | NL7502323A (en, 2012) |
| SE (1) | SE7502252L (en, 2012) |
| SU (1) | SU603339A3 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2831871A1 (de) * | 1978-07-20 | 1980-02-07 | Basf Ag | Halogensubstituierte thiophen-verbindungen |
| US4235685A (en) * | 1979-09-04 | 1980-11-25 | Ethyl Corporation | Preparation of 3-thenyl bromide |
| GB8806584D0 (en) * | 1988-03-19 | 1988-04-20 | Interox Chemicals Ltd | Bromination |
| KR100612459B1 (ko) * | 2004-07-15 | 2006-08-16 | 동진기업 주식회사 | 식음료용 포장용기 |
| EP3444243B1 (en) * | 2016-03-31 | 2020-09-02 | FUJIFILM Toyama Chemical Co., Ltd. | Method for producing 5-(bromomethyl)-1-benzothiophene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3190825A (en) * | 1961-07-19 | 1965-06-22 | Dow Chemical Co | Bromination of aromatic compounds |
-
1974
- 1974-02-28 GB GB9116/74A patent/GB1483349A/en not_active Expired
-
1975
- 1975-02-19 IE IE339/75A patent/IE41774B1/en unknown
- 1975-02-21 BE BE153609A patent/BE825833A/xx unknown
- 1975-02-21 US US05/551,525 patent/US3947336A/en not_active Expired - Lifetime
- 1975-02-25 ES ES435064A patent/ES435064A1/es not_active Expired
- 1975-02-26 DE DE19752508335 patent/DE2508335A1/de active Pending
- 1975-02-26 HU HU75SI00001457A patent/HU173013B/hu unknown
- 1975-02-27 CH CH249075A patent/CH597213A5/xx not_active IP Right Cessation
- 1975-02-27 CA CA221,184A patent/CA1036099A/en not_active Expired
- 1975-02-27 NL NL7502323A patent/NL7502323A/xx not_active Application Discontinuation
- 1975-02-27 SE SE7502252A patent/SE7502252L/xx unknown
- 1975-02-27 SU SU752111077A patent/SU603339A3/ru active
- 1975-02-27 IT IT48369/75A patent/IT1029881B/it active
- 1975-02-28 FR FR7506371A patent/FR2262651B1/fr not_active Expired
- 1975-02-28 JP JP50025518A patent/JPS50123657A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IE41774L (en) | 1975-08-28 |
| CH597213A5 (en, 2012) | 1978-03-31 |
| BE825833A (fr) | 1975-08-21 |
| CA1036099A (en) | 1978-08-08 |
| IE41774B1 (en) | 1980-03-26 |
| JPS50123657A (en, 2012) | 1975-09-29 |
| FR2262651A1 (en, 2012) | 1975-09-26 |
| US3947336A (en) | 1976-03-30 |
| IT1029881B (it) | 1979-03-20 |
| HU173013B (hu) | 1979-01-28 |
| ES435064A1 (es) | 1976-12-16 |
| FR2262651B1 (en, 2012) | 1978-04-21 |
| NL7502323A (nl) | 1975-09-01 |
| DE2508335A1 (de) | 1975-09-04 |
| SE7502252L (en, 2012) | 1975-08-29 |
| GB1483349A (en) | 1977-08-17 |
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