KR850004464A - 디플루오로피리딘 화합물의 제조방법 - Google Patents
디플루오로피리딘 화합물의 제조방법 Download PDFInfo
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- KR850004464A KR850004464A KR1019840008270A KR840008270A KR850004464A KR 850004464 A KR850004464 A KR 850004464A KR 1019840008270 A KR1019840008270 A KR 1019840008270A KR 840008270 A KR840008270 A KR 840008270A KR 850004464 A KR850004464 A KR 850004464A
- Authority
- KR
- South Korea
- Prior art keywords
- beta
- compound
- formula
- product
- gamma
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 23
- -1 difluoropyridine compound Chemical class 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 9
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000003444 phase transfer catalyst Substances 0.000 claims 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- 150000004673 fluoride salts Chemical class 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- BBHYMJRPJFVNPI-UHFFFAOYSA-N 2,3,5-tribromopyridine Chemical compound BrC1=CN=C(Br)C(Br)=C1 BBHYMJRPJFVNPI-UHFFFAOYSA-N 0.000 claims 1
- CNLIIAKAAMFCJG-UHFFFAOYSA-N 2,3,5-trichloropyridine Chemical compound ClC1=CN=C(Cl)C(Cl)=C1 CNLIIAKAAMFCJG-UHFFFAOYSA-N 0.000 claims 1
- ABNQGNFVSFKJGI-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=C(Cl)C(Cl)=C1 ABNQGNFVSFKJGI-UHFFFAOYSA-N 0.000 claims 1
- XIFCGIKPAAZFFS-UHFFFAOYSA-N 2,3-difluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC(C(F)(F)F)=CN=C1F XIFCGIKPAAZFFS-UHFFFAOYSA-N 0.000 claims 1
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 claims 1
- MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 claims 1
- GDSROTVTTLUHCO-UHFFFAOYSA-N 3-chloro-2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=NC=C(C(F)(F)F)C=C1Cl GDSROTVTTLUHCO-UHFFFAOYSA-N 0.000 claims 1
- QVIQXJRQVOPYGI-UHFFFAOYSA-N 5-bromo-2,3-difluoropyridine Chemical compound FC1=CC(Br)=CN=C1F QVIQXJRQVOPYGI-UHFFFAOYSA-N 0.000 claims 1
- PERMDYZFNQIKBL-UHFFFAOYSA-N 5-chloro-2,3-difluoropyridine Chemical compound FC1=CC(Cl)=CN=C1F PERMDYZFNQIKBL-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000003983 crown ethers Chemical class 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (23)
- 알파-또는 감마-할로-치환된 베타-할로피리딘을 유효량의 KF 또는 CsF와 액체매질중의 반응조건하에 접촉반응시키는 한편, 베타-플루오로피리딘 생성물을 주로 형성된 그대로 분리시키고, 임의로, 생성물인 베타-플루오로피리딘의 분리속도에 따라 알파-또는 감마-할로-치환된 베타-할로피리딘을 가하여, 베타-할로피리딘 화합물로부터 베타-플루오로피리딘 화합물을 제조하는 방법.
- 제 1 항에 있어서, 알파-또는 감마-할로-치환체가 불소인 방법.
- 제 1 항에 있어서, 알파-또는 감마-할로-치환체가 염소이고, 생성물이 알파, 베타-또는 베타, 감마-디플루오로피리딘 화합물인 방법.
- 제 2 항에 있어서, 베타-치환체가 염소인 방법.
- 제 3 항에 있어서, 베타-치환체가 염소이고 생성물이 알파, 베타-또는 베타 감마-디플루오로피리딘 화합물인 방법.
- 제 1 항에 있어서, 알파-할로-치환된 베타-할로피리딘 화합물이 일반식(V)의 화합물이고 베타-플루오로피리딘 생성물이 일반식(VI)의 화합물이거나, 감마-할로-치환된 베타-할로피리딘 화합물이 일반식(VII)의 화합물이고 베타-플루오로피리딘 생성물이 일반식(VIII)의 화합물인 방법.상기식에서, Hal은 C1,Br 또는 I이고, X는 F 또는 Ha1이고, A및 B는 각기 H, CH3,CF3,F 또는 Hal이고, R은 H, CF3, CH3, F, Hal 또는 CN이고, Y는 A 또는 F이며, 단 A가 Hal 경우 Y는 F이고, Z는 B 또는F이며, 단 B가 Hal인 경우 Z는 F이고, S는 R 또는 F이며, 단 R이 Ha1이고 A 또는 B가 F 또는 Ha1 인 경우 S는 F이다.
- 제 6 항에 있어서, Ha1이 Cl인 방법.
- 제 6 항에 있어서, Hal이 Br인 방법.
- 제 6 항에 있어서, R이 CF3인 방법.
- 제 6 항에 있어서, R이 Br인 방법.
- 제 6 항에 있어서, R이 C1인 방법.
- 제 6 항에 있어서, 일반식(V)의 화합물이 3-클로로-2-플루오로-5-(트리플루오로메틸)피리딘이고 생성물(VI)이 2,3-디플루오로-5-(트리플루오로메틸)피리딘인 방법.
- 제 6 항에 있어서, 일반식(V)의 화합물이 2,3-디클로로-5-(트리플루오로메틸)피리딘인 방법.
- 제 6 항에 있어서, 일반식(V)의 화합물이 2,3,5-트리클로로피리딘이고 생성물(VI)가 2,3-디플루오로-5-클로로피리딘인 방법.
- 제 6 항에 있어서, 일반식(V)의 화합물이 2,3,5-트리브로모피리딘이고 생성물(VI)가 2,3-디플루오로-5-브로모피리딘인 방법.
- 제 6 항에 있어서, 플루오라이드염이 KF이고, 반응이 (a)상-전이촉매 및 임의로 (b)산소캐빈저 존재하에 수행되는 방법.
- 제 6 항에 있어서, 액체 반응매질이 극성 비양자성 희석제인 방법.
- 제 17 항에 있어서, 희석제가 디메틸설폭사이드, 설폴란 또는 N-메틸피롤리디논인 방법.
- 제 18 항에 있어서, 플루오라이드염이 CsF이고 반응온도가 70 내지 150℃인 방법.
- 제 6 항에 있어서, 염이 KF이고 반응온도가 175℃ 내지 희석제의 비점인 방법.
- 제 19 항에 있어서, 반응이 50 내지 300mmHg의 압력하에 수행되는 방법.
- 제 19 항에 있어서, 반응이 (a) 상-전이 촉매 존재하 및, 임의로 (b) 산 스캐빈저 존재하에 수행되는 방법.
- 제 22 항에 있어서, 상-전이 촉매가 4급 암모늄 할라이드, 크라운 에테르 또는 트리스(3,6-디옥사헵틸)아민인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56480083A | 1983-12-23 | 1983-12-23 | |
| US564,800 | 1983-12-23 | ||
| US66558884A | 1984-10-29 | 1984-10-29 | |
| US665588 | 1984-10-29 | ||
| US665,588 | 1984-10-29 | ||
| US564800 | 2000-05-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850004464A true KR850004464A (ko) | 1985-07-15 |
| KR900004039B1 KR900004039B1 (ko) | 1990-06-09 |
Family
ID=27073665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840008270A KR900004039B1 (ko) | 1983-12-23 | 1984-12-22 | 디플루오로피리딘 화합물의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0146924B1 (ko) |
| JP (1) | JPS60156672A (ko) |
| KR (1) | KR900004039B1 (ko) |
| AU (1) | AU566757B2 (ko) |
| CA (1) | CA1292746C (ko) |
| DE (1) | DE3478598D1 (ko) |
| DK (1) | DK160489C (ko) |
| ES (1) | ES8607937A1 (ko) |
| HU (1) | HU199121B (ko) |
| IL (1) | IL73807A (ko) |
| PL (1) | PL251146A1 (ko) |
| RO (1) | RO90047A (ko) |
| SU (1) | SU1376942A3 (ko) |
| TR (1) | TR22146A (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4746744A (en) * | 1986-10-22 | 1988-05-24 | The Dow Chemical Company | Method of preparation of 3,5-dichloro-2,4,6-trifluoropyridine |
| DE59309922D1 (de) * | 1992-02-20 | 2000-02-17 | Clariant Gmbh | Verfahren zur Herstellung von substituierten 2,3-Difluorpyridinen |
| US5650517A (en) * | 1994-11-01 | 1997-07-22 | Ciba-Geigy Corporation | Process for the preparation of 2,3-difluoro-5-halopyridines |
| DE19745212A1 (de) * | 1997-10-13 | 1999-04-15 | Clariant Gmbh | Verfahren zur Herstellung von fluorierten aromatischen Verbindungen |
| JP5589778B2 (ja) | 2010-11-05 | 2014-09-17 | 日立金属株式会社 | 差動信号伝送用ケーブルと回路基板の接続構造及び接続方法 |
| BR102014028164A2 (pt) | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| TW201609652A (zh) | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（三） |
| TW201609651A (zh) | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（一） |
| TWI726900B (zh) | 2015-08-04 | 2021-05-11 | 美商陶氏農業科學公司 | 用於氟化化合物之過程 |
| EP4311828A1 (en) * | 2022-07-26 | 2024-01-31 | Basf Se | A process for the photolytic chlorination of 3-halopyridine with molecular chlorine |
| WO2023241960A1 (en) * | 2022-06-15 | 2023-12-21 | Basf Se | A process for the photolytic chlorination of 3-halopyridine with molecular chlorine |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1039987A (en) * | 1964-03-17 | 1966-08-24 | Pennwalt Corp | Fluoropyridines |
| US4031100A (en) * | 1976-08-23 | 1977-06-21 | The Dow Chemical Company | Process for making 2,6-difluoropyridine |
| ATE14307T1 (de) * | 1981-04-27 | 1985-08-15 | Ici Plc | Verfahren zur herstellung von fluormethylpyridinen und bestimmte auf diese weise erhaltene verbindungen. |
| IL68822A (en) * | 1982-06-18 | 1990-07-12 | Dow Chemical Co | Pyridyl(oxy/thio)phenoxy compounds,herbicidal compositions and methods of using them |
| US4480102A (en) * | 1982-07-23 | 1984-10-30 | The Dow Chemical Company | 2,3-Difluoro-5-(trifluoromethyl)pyridine and methods of making and using the same |
| DE3478681D1 (en) * | 1983-02-18 | 1989-07-20 | Nippon Catalytic Chem Ind | Organic fluorine compounds |
-
1984
- 1984-12-10 CA CA000469676A patent/CA1292746C/en not_active Expired - Fee Related
- 1984-12-11 AU AU36502/84A patent/AU566757B2/en not_active Ceased
- 1984-12-12 IL IL73807A patent/IL73807A/xx not_active IP Right Cessation
- 1984-12-19 DE DE8484115856T patent/DE3478598D1/de not_active Expired
- 1984-12-19 EP EP84115856A patent/EP0146924B1/en not_active Expired
- 1984-12-20 ES ES538891A patent/ES8607937A1/es not_active Expired
- 1984-12-21 PL PL25114684A patent/PL251146A1/xx unknown
- 1984-12-21 DK DK624184A patent/DK160489C/da not_active IP Right Cessation
- 1984-12-21 SU SU843834156A patent/SU1376942A3/ru active
- 1984-12-21 TR TR22146A patent/TR22146A/xx unknown
- 1984-12-21 HU HU844791A patent/HU199121B/hu not_active IP Right Cessation
- 1984-12-22 KR KR1019840008270A patent/KR900004039B1/ko not_active IP Right Cessation
- 1984-12-22 RO RO84116822A patent/RO90047A/ro unknown
- 1984-12-24 JP JP59272724A patent/JPS60156672A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES538891A0 (es) | 1986-01-01 |
| DK624184D0 (da) | 1984-12-21 |
| EP0146924A2 (en) | 1985-07-03 |
| HUT36459A (en) | 1985-09-30 |
| AU3650284A (en) | 1985-06-27 |
| SU1376942A3 (ru) | 1988-02-23 |
| JPH0586385B2 (ko) | 1993-12-10 |
| CA1292746C (en) | 1991-12-03 |
| DK160489B (da) | 1991-03-18 |
| EP0146924A3 (en) | 1986-03-12 |
| DE3478598D1 (en) | 1989-07-13 |
| JPS60156672A (ja) | 1985-08-16 |
| ES8607937A1 (es) | 1986-01-01 |
| AU566757B2 (en) | 1987-10-29 |
| DK160489C (da) | 1991-09-16 |
| TR22146A (tr) | 1986-08-17 |
| KR900004039B1 (ko) | 1990-06-09 |
| PL251146A1 (en) | 1985-10-22 |
| EP0146924B1 (en) | 1989-06-07 |
| HU199121B (en) | 1990-01-29 |
| RO90047A (ro) | 1986-09-30 |
| IL73807A0 (en) | 1985-03-31 |
| DK624184A (da) | 1985-06-24 |
| IL73807A (en) | 1988-05-31 |
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