DD152537A5 - Verfahren zur herstellung von 4-fluor-3-phenoxy-toluol - Google Patents

Verfahren zur herstellung von 4-fluor-3-phenoxy-toluol Download PDF

Info

Publication number: DD152537A5
Authority: DD; German Democratic Republic
Prior art keywords: fluoro; toluene; copper; phenoxy; preparation
Prior art date: 1979-08-08

Application number

DD80223103A

Other languages

German (de)

English (en)

Inventor

Rainer Fuchs

Fritz Maurer

Uwe Priesnitz

Hans-Jochem Riebel

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1979-08-08

Filing date

1980-08-05

Publication date

1981-12-02

1980-08-05 Application filed by Bayer Ag filed Critical Bayer Ag

1981-12-02 Publication of DD152537A5 publication Critical patent/DD152537A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title claims abstract description 6
ILKFYEKKPVEUOK-UHFFFAOYSA-N 1-fluoro-4-methyl-2-phenoxybenzene Chemical compound CC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 ILKFYEKKPVEUOK-UHFFFAOYSA-N 0.000 title claims abstract description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims abstract description 12
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052802 copper Inorganic materials 0.000 claims abstract description 8
239000010949 copper Substances 0.000 claims abstract description 8
239000003513 alkali Substances 0.000 claims abstract description 7
239000003054 catalyst Substances 0.000 claims abstract description 7
239000005749 Copper compound Substances 0.000 claims abstract description 5
150000001880 copper compounds Chemical class 0.000 claims abstract description 5
QLRKALMVPCQTMU-UHFFFAOYSA-N 2-bromo-1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C(Br)=C1 QLRKALMVPCQTMU-UHFFFAOYSA-N 0.000 claims abstract description 4
239000002671 adjuvant Substances 0.000 claims abstract description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 4
-1 alkaline earth metal carbonates Chemical class 0.000 claims abstract 2
239000003085 diluting agent Substances 0.000 claims description 3
150000001342 alkaline earth metals Chemical class 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 3
239000001095 magnesium carbonate Substances 0.000 description 3
229910000021 magnesium carbonate Inorganic materials 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
150000004707 phenolate Chemical class 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
229940031826 phenolate Drugs 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
CJKXKPCJTQPOMZ-UHFFFAOYSA-N 1-bromo-2,3,4-trifluoro-5-methoxybenzene Chemical class COC1=CC(Br)=C(F)C(F)=C1F CJKXKPCJTQPOMZ-UHFFFAOYSA-N 0.000 description 1
KGCDGLXSBHJAHZ-UHFFFAOYSA-N 1-chloro-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Cl)C(F)=C1F KGCDGLXSBHJAHZ-UHFFFAOYSA-N 0.000 description 1
RJCGZNCCVKIBHO-UHFFFAOYSA-N 1-chloro-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1 RJCGZNCCVKIBHO-UHFFFAOYSA-N 0.000 description 1
PGPNJCAMHOJTEF-UHFFFAOYSA-N 1-chloro-4-phenoxybenzene Chemical compound C1=CC(Cl)=CC=C1OC1=CC=CC=C1 PGPNJCAMHOJTEF-UHFFFAOYSA-N 0.000 description 1
WRWPPGUCZBJXKX-UHFFFAOYSA-N 1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C=C1 WRWPPGUCZBJXKX-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
AHJRONLVHNFUNH-UHFFFAOYSA-N 2-bromo-1,3,4,5-tetrafluorobenzene Chemical compound FC1=CC(F)=C(Br)C(F)=C1F AHJRONLVHNFUNH-UHFFFAOYSA-N 0.000 description 1
UAKARWYDBWHDOG-UHFFFAOYSA-N 2-bromo-4-methyl-1-phenoxybenzene Chemical compound BrC1=CC(C)=CC=C1OC1=CC=CC=C1 UAKARWYDBWHDOG-UHFFFAOYSA-N 0.000 description 1
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000001987 diarylethers Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
150000008423 fluorobenzenes Chemical class 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
239000003999 initiator Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
KRPXAHXWPZLBKL-UHFFFAOYSA-L magnesium;diphenoxide Chemical compound [Mg+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 KRPXAHXWPZLBKL-UHFFFAOYSA-L 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
239000000047 product Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
GMKSUTIIASULKI-UHFFFAOYSA-M sodium;2,3,4,5,6-pentafluorophenolate Chemical compound [Na+].[O-]C1=C(F)C(F)=C(F)C(F)=C1F GMKSUTIIASULKI-UHFFFAOYSA-M 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD80223103A 1979-08-08 1980-08-05 Verfahren zur herstellung von 4-fluor-3-phenoxy-toluol DD152537A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792932093 DE2932093A1 (de)	1979-08-08	1979-08-08	Verfahren zur herstellung von 4-fluor- 3-phenoxy-toluol

Publications (1)

Publication Number	Publication Date
DD152537A5 true DD152537A5 (de)	1981-12-02

Family

ID=6077896

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80223103A DD152537A5 (de)	1979-08-08	1980-08-05	Verfahren zur herstellung von 4-fluor-3-phenoxy-toluol

Country Status (9)

Country	Link
US (1)	US4316994A (da)
EP (1)	EP0024019B1 (da)
JP (1)	JPS5626828A (da)
BR (1)	BR8004974A (da)
DD (1)	DD152537A5 (da)
DE (2)	DE2932093A1 (da)
DK (1)	DK340680A (da)
HU (1)	HU182693B (da)
IL (1)	IL60756A0 (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3040849A1 (de) *	1980-10-30	1982-06-09	Hoechst Ag, 6000 Frankfurt	Verfahren zur herstellung von diphenylaethern
DE3602169A1 (de) *	1986-01-22	1987-07-23	Schering Ag	Neue alkan- und alkoxyalkanderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende insektizide und akarizide mittel
US4766253A (en) *	1987-05-04	1988-08-23	Ciba-Geigy Corporation	Process for preparing chlorinated diphenyl ethers
FR2669923B1 (fr) *	1990-11-29	1993-01-29	Rhone Poulenc Chimie	Procede de preparation de composes aromatiques alkoxyles.
FR2669922A1 (fr) *	1990-11-29	1992-06-05	Rhone Poulenc Chimie	Procede de preparation de composes aromatiques alkoxyles.
US6395939B1 (en) *	1997-10-06	2002-05-28	Massachusetts Institute Of Technology	Diaryl ether condensation reactions

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PH18332A (en) *	1972-01-27	1985-05-31	Ishihara Sangyo Kaisha	Herbicide
DE2242519C2 (de)	1972-08-30	1982-03-18	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von gegebenenfalls im Kern substituierten chlorierten Diphenylethern
DE2745006A1 (de)	1977-10-06	1979-04-19	Bayer Ag	Substituierte diphenylaether, verfahren zu ihrer herstellung und ihre verwendung als entblaetterungsmittel
DE2837525A1 (de) *	1978-08-28	1980-03-20	Bayer Ag	Verfahren zur herstellung von 4- fluoro-3-phenoxy-toluol

1979
- 1979-08-08 DE DE19792932093 patent/DE2932093A1/de not_active Withdrawn
1980
- 1980-07-18 US US06/170,194 patent/US4316994A/en not_active Expired - Lifetime
- 1980-07-31 DE DE8080104527T patent/DE3060759D1/de not_active Expired
- 1980-07-31 EP EP80104527A patent/EP0024019B1/de not_active Expired
- 1980-08-05 DD DD80223103A patent/DD152537A5/de unknown
- 1980-08-05 IL IL60756A patent/IL60756A0/xx unknown
- 1980-08-06 JP JP10723280A patent/JPS5626828A/ja active Pending
- 1980-08-07 DK DK340680A patent/DK340680A/da not_active Application Discontinuation
- 1980-08-07 HU HU801966A patent/HU182693B/hu unknown
- 1980-08-07 BR BR8004974A patent/BR8004974A/pt unknown

Also Published As

Publication number	Publication date
IL60756A0 (en)	1980-10-26
JPS5626828A (en)	1981-03-16
US4316994A (en)	1982-02-23
HU182693B (en)	1984-02-28
BR8004974A (pt)	1981-02-17
EP0024019A1 (de)	1981-02-18
DE2932093A1 (de)	1981-02-26
DE3060759D1 (en)	1982-10-07
EP0024019B1 (de)	1982-08-11
DK340680A (da)	1981-02-09

Publication	Publication Date	Title
EP0008734B1 (de)	1981-07-29	Verfahren zur Herstellung von 4-Fluoro-3-phenoxy-toluol
EP0034741B1 (de)	1983-12-21	Verfahren zur Herstellung eines substituierten Bromfluorbenzols und 3-Brom-4-fluorbenzonitril
DE3888523T2 (de)	1994-06-23	Verfahren zur herstellung von 4,4'-dibromdiphenylether.
EP0024019B1 (de)	1982-08-11	Verfahren zur Herstellung von 4-Fluor-3-phenoxy-toluol
EP0234013B1 (de)	1990-09-19	Verfahren zur Herstellung von Perfluorcarbonsäuren
EP0302326B1 (de)	1992-04-15	Verfahren zur Herstellung von mit Fluor und gegebenenfalls zusätzlich Chlor substituierten Benzotrifluoriden und neue Benzotrifluoride
EP0124002B1 (de)	1986-11-12	Verfahren zur Herstellung von aromatischen Verbindungen, die über ein Heteroatom gebundene perfluorierte Seitenketten enthalten
DE3326875A1 (de)	1985-02-14	Neue fluorpivalsaeurefluoride und verfahren zu ihrer herstellung
DE3314249A1 (de)	1984-10-25	Verfahren zur herstellung von fluorierten phenylessigsaeureestern und neue fluorierte trichlorethylbenzole
DE2548970C3 (de)	1978-05-11	Verfahren zur Herstellung von Trichlormethyl-trifluormethyl-benzolen
DE3104259A1 (de)	1982-09-02	Verfahren zur herstellung von polychlorbenzoylchloriden
DE3029368C2 (da)	1990-12-13
EP0011208B1 (de)	1981-07-29	Verfahren zur Herstellung von 3-Phenoxy-benzaldehyden
EP0365914B1 (de)	1992-07-22	Neue Fluor enthaltende und an der CH3-Gruppe gegebenenfalls halogenierte Acetophenone und deren Herstellung aus neuen Fluor enthaltenden Benzonitrilen
EP0394644B1 (de)	1994-10-05	Halogenbenzolderivate
DE60133607T2 (de)	2009-05-20	Verfahren zur herstellung von allylchlorid
DE4123322C2 (de)	2003-04-03	2-Chlor-3,4,5-trifluorbenzoesäure 2,2'-Dichlor-3,4,5-trifluoracetophenon, 2,2',2'-Trichlor-3,4,5-trifluoracetophenon, 5,2'-Dichlor-2,3,4-trifluoracetophenon und 5,2',2'-Trichlor-2,3,4-trifluoracetophenon und Verfahren zur Herstellung dieser Verbindungen und der isomeren 5-Chlor-2,3,4-trifluorbenzoesäure
WO1995029886A1 (de)	1995-11-09	Verfahren zur herstellung brom enthaltender aromatischer verbindungen, neue brom enthaltende verbindungen und ihre verwendung als zwischenprodukte bei der synthese von wirkstoffen
WO2001077062A1 (de)	2001-10-18	Verfahren zur herstellung von 4-brom- und 4-chlor-2-nitro-1-trifluormethoxybenzol
EP0173153B1 (de)	1989-02-01	Neue benzokondensierte, fluorierte, heterocyclische Verbindungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung
DE3344870C2 (da)	1989-07-13
DE3111848A1 (de)	1982-10-14	Verfahren zur herstellung von substituierten (alpha)-halogen-propionsaeuren und ihren derivaten
DE3140634A1 (de)	1983-04-21	Verfahren zur herstellung von kernfluorierten benzoylfluoriden
DE2717673B2 (de)	1981-07-30	Verfahren zur Herstellung von (1-Chloräthenyl-)oxiran
DE2454326A1 (de)	1976-05-20	Perchlordiazafulven und ein verfahren zu seiner herstellung