GB1080167A - Improvements in or relating to the production of halogenated benzene derivatives - Google Patents
Improvements in or relating to the production of halogenated benzene derivativesInfo
- Publication number
- GB1080167A GB1080167A GB2387963A GB2387963A GB1080167A GB 1080167 A GB1080167 A GB 1080167A GB 2387963 A GB2387963 A GB 2387963A GB 2387963 A GB2387963 A GB 2387963A GB 1080167 A GB1080167 A GB 1080167A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lithium
- prepared
- converted
- difluorophenyl
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- LFGWEGCCZHIJLM-UHFFFAOYSA-N [Li]C1=C(F)C=CC=C1F Chemical compound [Li]C1=C(F)C=CC=C1F LFGWEGCCZHIJLM-UHFFFAOYSA-N 0.000 abstract 2
- -1 aryl lithium compound Chemical class 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 abstract 1
- VQBSSXXIODEGHF-UHFFFAOYSA-N 1,5-difluorocyclohexa-2,4-diene-1-carboxylic acid Chemical compound FC1(C(=O)O)CC(=CC=C1)F VQBSSXXIODEGHF-UHFFFAOYSA-N 0.000 abstract 1
- MRUDNSFOFOQZDA-UHFFFAOYSA-N 2,6-dichlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC=C1Cl MRUDNSFOFOQZDA-UHFFFAOYSA-N 0.000 abstract 1
- ODUZJBKKYBQIBX-UHFFFAOYSA-N 2,6-difluoroaniline Chemical compound NC1=C(F)C=CC=C1F ODUZJBKKYBQIBX-UHFFFAOYSA-N 0.000 abstract 1
- SOWRUJSGHKNOKN-UHFFFAOYSA-N 2,6-difluorobenzaldehyde Chemical compound FC1=CC=CC(F)=C1C=O SOWRUJSGHKNOKN-UHFFFAOYSA-N 0.000 abstract 1
- AVRQBXVUUXHRMY-UHFFFAOYSA-N 2,6-difluorobenzamide Chemical compound NC(=O)C1=C(F)C=CC=C1F AVRQBXVUUXHRMY-UHFFFAOYSA-N 0.000 abstract 1
- ONOTYLMNTZNAQZ-UHFFFAOYSA-N 2,6-difluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1F ONOTYLMNTZNAQZ-UHFFFAOYSA-N 0.000 abstract 1
- BNBRIFIJRKJGEI-UHFFFAOYSA-N 2,6-difluorobenzonitrile Chemical compound FC1=CC=CC(F)=C1C#N BNBRIFIJRKJGEI-UHFFFAOYSA-N 0.000 abstract 1
- QRHUZEVERIHEPT-UHFFFAOYSA-N 2,6-difluorobenzoyl chloride Chemical compound FC1=CC=CC(F)=C1C(Cl)=O QRHUZEVERIHEPT-UHFFFAOYSA-N 0.000 abstract 1
- CKKOVFGIBXCEIJ-UHFFFAOYSA-N 2,6-difluorophenol Chemical compound OC1=C(F)C=CC=C1F CKKOVFGIBXCEIJ-UHFFFAOYSA-N 0.000 abstract 1
- NHIZAYZZXMIFLW-UHFFFAOYSA-N 2-(2,6-difluorophenoxy)acetonitrile Chemical compound FC1=CC=CC(F)=C1OCC#N NHIZAYZZXMIFLW-UHFFFAOYSA-N 0.000 abstract 1
- HMRAGBUKCHZSFX-UHFFFAOYSA-N 2-(2,6-difluorophenyl)-1-phenylethanone Chemical compound FC1=CC=CC(F)=C1CC(=O)C1=CC=CC=C1 HMRAGBUKCHZSFX-UHFFFAOYSA-N 0.000 abstract 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 1
- WTAAOZZLCLUCIV-UHFFFAOYSA-N FC1(CC(=CC=C1)F)[Li] Chemical compound FC1(CC(=CC=C1)F)[Li] WTAAOZZLCLUCIV-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 150000002642 lithium compounds Chemical class 0.000 abstract 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000002002 slurry Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/26—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms
- C07C39/27—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms all halogen atoms being bound to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
2,6-Dihalogenophenyl lithium compounds are prepared by reacting a m-dihalogenobenzene with a lower alkyl or aryl lithium compound in an inert organic solvent, the temperature of the reaction mixture being maintained at - 50 DEG C. or lower. Other 2,6-dihalogenophenyl compounds are prepared therefrom by conventional methods. In Example 1, n-butyl lithium in tetrahydrofuran is reacted with m-difluorobenzene in tetrahydrofuran, and the solution of m-difluorophenyl lithium obtained is added to a slurry of solid CO2 in ether to form m-difluorobenzoic acid. This is converted via the azide into 2,6-difluoroaniline. In Example 2, 2,6-dichlorobenzoic acid is prepared. In Example 3,2,6-difluorophenyl lithium is treated with N-methyl formanilide at - 50 DEG C. and the product is hydrolysed to 2,6-difluorobenzaldehyde. In Example 4, 2,6-difluorophenyl lithium solution is reacted with trimethyl borate and the product hydrolysed to a boronic or boronic acid derivative which is oxidized by means of H2O2 to 2,6-difluoro-phenol. This is converted to 2-(21,61-difluorophenoxy)-ethylamine by reaction with chloroacetonitrile and reduction of the 2,6-difluorophenoxyacetonitrile formed with lithium aluminium hydride. The amine hydrochloride is refluxed with cyanamide and the product, treated with HNO3, yields 2 - (21,61 - difluorophenoxy)-ethyl guanidine nitrate. In Example 5, 2,6-difluorophenylacetophenone is prepared by the reaction of 2,6-difluorophenyl lithium with acetyl chloride and converted to its oxime. In Example 6, 2,6-difluorobenzoyl chloride and 2,6-difluorobenzamide are prepared from 2,6-difluorobenzoic acid and the amide converted to 2,6-difluorobenzonitrile by means of thionyl chloride.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2387963A GB1080167A (en) | 1963-06-14 | 1963-06-14 | Improvements in or relating to the production of halogenated benzene derivatives |
| GB3594665A GB1098387A (en) | 1963-06-14 | 1965-08-20 | Improvements in or relating to the production of halogenated benzene derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2387963A GB1080167A (en) | 1963-06-14 | 1963-06-14 | Improvements in or relating to the production of halogenated benzene derivatives |
| GB3594665A GB1098387A (en) | 1963-06-14 | 1965-08-20 | Improvements in or relating to the production of halogenated benzene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1080167A true GB1080167A (en) | 1967-08-23 |
Family
ID=26256772
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2387963A Expired GB1080167A (en) | 1963-06-14 | 1963-06-14 | Improvements in or relating to the production of halogenated benzene derivatives |
| GB3594665A Expired GB1098387A (en) | 1963-06-14 | 1965-08-20 | Improvements in or relating to the production of halogenated benzene derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3594665A Expired GB1098387A (en) | 1963-06-14 | 1965-08-20 | Improvements in or relating to the production of halogenated benzene derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB1080167A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0442340A2 (en) * | 1990-02-13 | 1991-08-21 | F. Hoffmann-La Roche Ag | Process for the preparation of an organolithium compound starting from 1,3-bis(trifluoromethyl)-benzene |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8331120D0 (en) * | 1983-11-22 | 1983-12-29 | Pfizer Ltd | Benzaldehyde derivatives |
| GB9319341D0 (en) * | 1993-09-17 | 1993-11-03 | Wellcome Found | Novel process |
| JP5433996B2 (en) * | 2008-07-10 | 2014-03-05 | Ｄｉｃ株式会社 | Method for producing fluorophenol derivative |
-
1963
- 1963-06-14 GB GB2387963A patent/GB1080167A/en not_active Expired
-
1965
- 1965-08-20 GB GB3594665A patent/GB1098387A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0442340A2 (en) * | 1990-02-13 | 1991-08-21 | F. Hoffmann-La Roche Ag | Process for the preparation of an organolithium compound starting from 1,3-bis(trifluoromethyl)-benzene |
| EP0442340A3 (en) * | 1990-02-13 | 1992-01-22 | F. Hoffmann-La Roche Ag | Process for the preparation of an organolithium compound starting from 1,3-bis(trifluoromethyl)-benzene |
| US5162577A (en) * | 1990-02-13 | 1992-11-10 | Hoffmann-La Roche Inc. | Process for lithiation of 1,3-bis(trifluoromethyl)benzene |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1098387A (en) | 1968-01-10 |
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