CS248745B2 - Production method of the 3-chlorine-2-fluor-5-/trifluormethyl/pyridine - Google Patents
Production method of the 3-chlorine-2-fluor-5-/trifluormethyl/pyridine Download PDFInfo
- Publication number
- CS248745B2 CS248745B2 CS854063A CS406385A CS248745B2 CS 248745 B2 CS248745 B2 CS 248745B2 CS 854063 A CS854063 A CS 854063A CS 406385 A CS406385 A CS 406385A CS 248745 B2 CS248745 B2 CS 248745B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen fluoride
- pyridine
- pressure
- reaction
- kpa
- Prior art date
Links
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 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 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 21
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 239000007791 liquid phase Substances 0.000 abstract description 7
- XVBWGQSXLITICX-UHFFFAOYSA-N 2,3-dichloro-5-(trichloromethyl)pyridine Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=CN=C1Cl XVBWGQSXLITICX-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 7
- -1 3-chloro-2-fluoro-5- (trifluoromethyl) pyrimidine Chemical compound 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- WEUYAMKLKASVNH-UHFFFAOYSA-N 1-(trifluoromethyl)pyridin-1-ium Chemical class FC(F)(F)[N+]1=CC=CC=C1 WEUYAMKLKASVNH-UHFFFAOYSA-N 0.000 description 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 description 1
- KAQJMEHRXVENSF-UHFFFAOYSA-N 2-(trichloromethyl)pyridine Chemical class ClC(Cl)(Cl)C1=CC=CC=N1 KAQJMEHRXVENSF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 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
- C07D213/60—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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/618,806 US4547577A (en) | 1984-06-08 | 1984-06-08 | Preparation of (trifluoromethyl)pyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS248745B2 true CS248745B2 (en) | 1987-02-12 |
Family
ID=24479217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS854063A CS248745B2 (en) | 1984-06-08 | 1985-06-06 | Production method of the 3-chlorine-2-fluor-5-/trifluormethyl/pyridine |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4547577A (ja) |
| EP (1) | EP0164104B1 (ja) |
| JP (1) | JPH0625111B2 (ja) |
| AU (1) | AU570801B2 (ja) |
| BR (1) | BR8502718A (ja) |
| CA (1) | CA1199331A (ja) |
| CS (1) | CS248745B2 (ja) |
| DE (1) | DE3585702D1 (ja) |
| DK (1) | DK159422C (ja) |
| HU (1) | HU199122B (ja) |
| SU (1) | SU1473711A3 (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0063872B1 (en) * | 1981-04-27 | 1985-07-17 | Imperial Chemical Industries Plc | Process for the preparation of fluoromethyl pyridines and certain novel products obtained therefrom |
| US4782161A (en) * | 1987-10-21 | 1988-11-01 | The Dow Chemical Company | Preparation of fluoropyridines |
| US4999432A (en) * | 1989-08-28 | 1991-03-12 | Dowelanco | Fluorination with hydrogen fluoride |
| CN107954924A (zh) * | 2016-10-18 | 2018-04-24 | 内蒙古佳瑞米精细化工有限公司 | 一种2-氟-3-氯-5-三氟甲基吡啶的制备方法 |
| CN107935920A (zh) * | 2017-11-30 | 2018-04-20 | 山东汇盟生物科技有限公司 | 2‑氟‑3‑氯‑5‑三氟甲基吡啶的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1039987A (en) * | 1964-03-17 | 1966-08-24 | Pennwalt Corp | Fluoropyridines |
| GB1272475A (en) * | 1969-05-30 | 1972-04-26 | Ici Ltd | Manufacture of fluoropyridines |
| DE2862492D1 (en) * | 1977-08-12 | 1988-09-01 | Ici Plc | Herbicidal halogenomethyl--pyridyloxy-phenoxy-alkanecarboxylic acids and derivatives, and processes of controlling unwanted plants therewith |
| JPS5461183A (en) * | 1977-10-21 | 1979-05-17 | Ishihara Sangyo Kaisha Ltd | 2-substituted-5-trifluoromethyl pyridine compounds |
| JPS55158979A (en) * | 1979-05-29 | 1980-12-10 | Seiko Epson Corp | Ink jet recording head |
| EP0074192B1 (en) * | 1981-09-03 | 1986-12-30 | Imperial Chemical Industries Plc | Chloro-trifluoromethyl pyridines |
| US4567273A (en) * | 1982-04-16 | 1986-01-28 | The Dow Chemical Company | Liquid phase halogen exchange of (trichloromethyl) pyridines to (trifluoromethyl)pyridines |
| US4493932A (en) * | 1982-09-13 | 1985-01-15 | The Dow Chemical Company | Chlorine exchange for fluorine in 2-fluoro-pyridine compounds |
| IL70307A (en) * | 1982-11-26 | 1987-02-27 | Dow Chemical Co | Preparation of(trifluoromethyl)pyridines |
-
1984
- 1984-06-08 US US06/618,806 patent/US4547577A/en not_active Expired - Lifetime
-
1985
- 1985-05-09 CA CA000481126A patent/CA1199331A/en not_active Expired
- 1985-05-21 AU AU42712/85A patent/AU570801B2/en not_active Ceased
- 1985-06-04 DE DE8585106917T patent/DE3585702D1/de not_active Expired - Lifetime
- 1985-06-04 EP EP85106917A patent/EP0164104B1/en not_active Expired - Lifetime
- 1985-06-05 BR BR8502718A patent/BR8502718A/pt not_active IP Right Cessation
- 1985-06-06 CS CS854063A patent/CS248745B2/cs unknown
- 1985-06-06 DK DK255485A patent/DK159422C/da not_active IP Right Cessation
- 1985-06-07 HU HU852275A patent/HU199122B/hu unknown
- 1985-06-07 JP JP60124064A patent/JPH0625111B2/ja not_active Expired - Fee Related
- 1985-06-07 SU SU853919403A patent/SU1473711A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0625111B2 (ja) | 1994-04-06 |
| EP0164104B1 (en) | 1992-03-25 |
| US4547577A (en) | 1985-10-15 |
| DK159422C (da) | 1991-03-18 |
| EP0164104A3 (en) | 1988-08-03 |
| JPS611662A (ja) | 1986-01-07 |
| AU570801B2 (en) | 1988-03-24 |
| HU199122B (en) | 1990-01-29 |
| EP0164104A2 (en) | 1985-12-11 |
| SU1473711A3 (ru) | 1989-04-15 |
| DE3585702D1 (de) | 1992-04-30 |
| DK255485A (da) | 1985-12-09 |
| CA1199331A (en) | 1986-01-14 |
| DK159422B (da) | 1990-10-15 |
| DK255485D0 (da) | 1985-06-06 |
| BR8502718A (pt) | 1986-02-12 |
| AU4271285A (en) | 1985-12-12 |
| HUT38316A (en) | 1986-05-28 |
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