DE3887603T2 - Chemisches Verfahren. - Google Patents

Chemisches Verfahren.

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Publication number
DE3887603T2
DE3887603T2 DE3887603T DE3887603T DE3887603T2 DE 3887603 T2 DE3887603 T2 DE 3887603T2 DE 3887603 T DE3887603 T DE 3887603T DE 3887603 T DE3887603 T DE 3887603T DE 3887603 T2 DE3887603 T2 DE 3887603T2
Authority
DE
Germany
Prior art keywords
mixture
ether
methyl ester
general formula
acid methyl
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 - Fee Related
Application number
DE3887603T
Other languages
English (en)
Other versions
DE3887603D1 (de
Inventor
Kevin Beautement
John Martin Clough
Christopher Richard Ay Godfrey
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Syngenta Ltd
Original Assignee
Zeneca Ltd
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.)
Filing date
Publication date
Priority claimed from GB878721221A external-priority patent/GB8721221D0/en
Priority claimed from GB878722537A external-priority patent/GB8722537D0/en
Priority claimed from GB888804433A external-priority patent/GB8804433D0/en
Application filed by Zeneca Ltd filed Critical Zeneca Ltd
Application granted granted Critical
Publication of DE3887603D1 publication Critical patent/DE3887603D1/de
Publication of DE3887603T2 publication Critical patent/DE3887603T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
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    • A01N41/06—Sulfonic acid amides
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    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
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    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
    • 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
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    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
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    • C07C67/00—Preparation of carboxylic acid esters
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
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    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
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Description

  • Die Erfindung bezieht sich auf ein Verfahren zur Herstellung van Propensäure-Derivaten, die als Fungicide oder als chemische Zwischenprodukte bei der Herstellung van Fungiciden brauchbar sind.
  • Gegenstand der Erfindung ist ein Verfahren zur Herstellung einer Verbindung der allgemeinen Formel (I),
  • worin die Benzolringe M und N gegebenenfalls einen oder mehrere Substituenten tragen, die unter den Bedingungen des Verfahrens nicht reaktiv sind, bei welchem eine Verbindung der allgemeinen Formel (II),
  • worin X für Halogen (vorzugsweise Jod, Chlor oder Brom) steht, mit einem Phenol der allgemeinen Formel (III)
  • in Gegenwart einer Base oder aber mit einem Salz des Phenols (III) umgesetzt wird, und zwar vorzugsweise in Gegenwart eines Katalysators, der ein geeignetes Übergangsmetall, ein Übergangsmetallsalz oder eine Übergangsmetallverbindung oder ein Gemisch davon enthält.
  • Bei diesem Verfahren können Verbindungen der allgemeinen Formel (I) erhalten werden durch Umsetzung von Verbindungen (II) mit Salzen, die sich von Phenolen der allgemeinen Formel (III) ableiten, indem die Phenole vorher mit einer Base umgesetzt werden. Bei dieser Ausführungsform der Erfindung ist die zusätzliche Anwesenheit einer Base während der Kupplungsreaktion nicht erforderlich.
  • Bei der Durchführung des erfindungsgemäßen Verfahrens kann ein Lösungsmittel verwendet werden. Geeignete Lösungsmittel sind solche, in denen beide Verbindungen (II) und (III) (oder davon abgeleitete Salze) löslich oder teilweise löslich sind und die unter den Reaktionsbedingungen mit keinem dieser Substrate reagieren. Lösungsmittel, die verwendet werden können, sind z.B. dipolare aprotische Lösungsmittel, z.B. N,N-Dimethylformamid, Dimethylsulfoxid, N,N-Dimethylacetamid und Methyl-isobutyl-keton. Wenn eines der Substrate unter den Reaktionsbedingungen eine Flüssigkeit ist, dann kann es in gewissen Fällen möglich sein, die Reaktion in Abwesenheit eines zugesetzten Lösungsmittels auszuführen.
  • Geeignete Basen für die Verwendung beim Verfahren sind solche, die entweder durch Abziehen des phenolischen Protons der Verbindung (III) vor der Reaktion mit dem Substrat (II) oder durch Neutralisation irgendeiner während der Reaktion gebildeten Saure reagieren, ohne daß sie aber wesentlich mit dem Substrat (II) oder dem Produkt (I) reagieren. Ein Beispiel für eine solche Base ist wasserfreies Kaliumcarbonat.
  • Geeignete Übergangsmetalle oder Übergangsmetallsalze oder Übergangsmetallverbindungen, welche das Verfahren katalysieren, sind z.B. Kupfermetall, Kupfersalze und Kupferverbindungen sowie Nickelsalze und Nickelverbindungen, z.B. Kupferbronze und Kupfer(I)-chlorid, welche einzeln oder in Mischung verwendet werden können (siehe beispielsweise A. A. Moroz und M. S. Shvartsberg, Russian Chemical Reviews, 1974, 43 (8), 679-689).
  • Das Verfahren kann innerhalb eines großen Temperaturbereichs ausgeführt werden. In der Praxis wird die Temperatur so gewählt, daß die Reaktion mit einer vernünftigen und zweckmäßigen Geschwindigkeit abläuft. Sie wird üblicherweise im Bereich von 100 bis 200ºC liegen, was von der Reaktivität der Substrate (II) und (III) und von der Natur des Katalysators abhängt.
  • Die Anwesenheit der Propenoat-Doppelbindung gibt zu geometrischen Isomeren der Verbindungen (I) und (II) Anlaß. Diese Isomere werden mit den üblicherweise verwendeten Termen (E) und (Z) gemäß dem Kahn-Ingold-Prelog-System bezeichnet, das ausführlich in der Literatur beschrieben ist (siehe beispielsweise J. March, "Advances Organic Chemistry", 3. Auflage, Wiley-Interscience, Seiten 109 ff.). Als Substrate beim erfindungsgemäßen Verfahren können entweder die (E)- oder die (Z)-Isomere der Verbindungen der allgemeinen Formel (II) oder Gemische davon verwendet werden. Unter den Reaktionsbedingungen erleidet das (Z)- Isomer der Verbindungen der allgemeinen Formel (II) üblicherweise eine Stereomutation zum entsprechenden (E)- Isomer, weshalb die Reaktion Verbindungen der allgemeinen Formel (I) mit der (E)-Geometrie ergibt. D.h. also, es werden Verbindungen der Formel (I) mit der (E)-Geometrie üblicherweise gebildet, unabhängig von der Geometrie der Vorläufer der Formel (II).
  • Das erfindungsgemäße Verfahren ist von besonderem Interesse bei der Herstellung von fungiciden Verbindungen, wie sie beispielsweise in EP-A-0 178 826 beschrieben sind, und zwar insbesondere solchen Verbindungen der allgemeinen Formel (IV),
  • worin A, B, D und Y, welche gleich oder verschieden sein können, für Wasserstoff- oder Halogenatome oder gegebenenfalls substituierte Alkyl-, gegebenenfalls substituierte Alkenyl-, gegebenenfalls substituierte Aryl-, gegebenenfalls substituierte Heteroaryl-, gegebenenfalls substituierte Alkinyl-, gegebenenfalls substituierte Alkoxy-, gegebenenfalls substituierte Aryloxy-, gegebenenfalls substituierte Heteroaryloxy-, gegebenenfalls substituierte Arylalkoxy-, gegebenenfalls substituierte Acyloxy-, gegebenenfalls substituierte Sulfonyloxy-, gegebenenfalls substituierte Amino-, gegebenenfalls substituierte Arylazo-, Acylamino-, Nitro-, Cyano-, -CO&sub2;R¹, -CONR²R³, -COR&sup4;, -CR&sup5;=NR&sup6; oder -N=CR&sup7;R&sup8; -Gruppen stehen, wobei die Gruppen A und B, wenn sie in Nachbarschaftsstellung am Phenylring liegen, auch verbunden sein können, um einen kondensierten Ring zu bilden, der gegebenenfalls ein oder mehrere Heteroatome enthält; wobei R¹, R², R³, R&sup4;, R&sup5;, R&sup6;, R&sup7; und R&sup8;, welche gleich oder verschieden sein können, für Wasserstoffatome oder Alkyl-, Cycloalkyl-, Alkenyl-, Alkinyl-, gegebenenfalls substituierte Aryl-, gegebenenfalls substituierte Heteroaryl-, gegebenenfalls substituierte Aralkyl- oder Cycloalkylalkyl-Gruppen stehen.
  • Das Verfahren kann auch zur Herstellung von chemischen Zwischenprodukten verwendet werden, die bei der Herstellung von Fungiciden brauchbar sind.
  • Substrate der allgemeinen Formel (II) kann durch das Verfahren hergestellt werden, das in EP-A-0 178 826 angegeben ist.
  • Verbindungen der allgemeinen Formel (III) können durch bekannte Verfahren hergestellt werden, die in der chemischen Literatur beschrieben sind.
  • Die folgenden Beispiele erläutern die Erfindung. In diesen Beispielen wurden die Reaktionen, bei denen wasserempfindliche Zwischenprodukte verwendet wurden, unter einer Stickstoffatmosphäre in trockenen Lösungsmitteln ausgeführt. Der Ausdruck "Ether" bezieht sich auf Diethylether. Magnesiumsulfat wurde zur Trocknung von Lösungen verwendet. Lösungen wurden unter vermindertem Druck konzentriert. Chromatographie wurde auf Silicagel-Kolonnen ausgeführt. Wenn nichts anderes angegeben ist, wurden die NMR-Spektren bei 270 MHz unter Verwendung von Deuteriochloroform-Lösungen und Tetramethylsilan als innerer Standard aufgenommen. Wenn angegeben, dann sind die spektroskopischen Daten selektiv. Es wurde kein Versuch gemacht, jede Absorption in allen Fällen aufzulisten.
  • Die folgenden Abkürzungen werden verwendet:
  • IR = Infrarot
  • NMR = magnetische Kernresonanz
  • MS = Massenspektroskopie
  • GC = Gaschromatographie
  • s - Singlett
  • d - Dublett
  • t = Triplett
  • m = Multiplett
  • br = breit
  • Fp = Schmelzpunkt
  • ppm = Teile je Million
  • DMF = N,N-Dimethylformamid
    • Beispiel 1
  • Dieses Beispiel erläutert die Synthese von (E)-3-Methoxy- 2-[2-(3-methylphenoxy) phenyl]propensäure-methylester.
  • Eine Lösung von ortho-Bromophenylessigsäure (5,14 g) in trockenem Methanol (40 ml), die 5 Tropfen konzentrierte Schwefelsäure enthielten, wurde 3 h auf Rückfluß erhitzt. Das Reaktionsgemisch wurde abgekühlt und dann in Eiswasser (150 ml) geschüttet und mit Ether (2 x 75 ml) extrahiert. Die Etherschichten wurden vereinigt, aufeinanderfolgend mit Wasser (3 x) gesättigter Natriumbicarbonatlösung (2 x), Wasser (1 x) und dann mit gesättigter Kochsalzlösung gewaschen und getrocknet. Filtration und Eindampfung ergab ortho-Bromophenylessigsäure-methylester (5,23 g, 96 %) als blaßgelbe Flüssigkeit; IR-Maximum 1742 cm&supmin;¹. Das Produkt wurde ohne weitere Reinigung verwendet,
  • Ein Gemisch aus ortho-Bromophenylessigsäure-methylester (5,23 g) und Methylformiat (27,46 g) in DMF (6 ml) wurde tropfenweise zu einer gerührten Suspension von Natriumhydrid (1,10 g) in DMF (45 ml) bei 0 bis 5ºC (Schäumen) zugegeben. Nachdem Dünnschichtchromatographie gezeigt hatte, daß die Reaktion zu Ende war, wurde das Gemisch in Wasser geschüttet, angesäuert und mit Ether extrahiert. Die Extrakte wurden getrocknet und konzentriert, wobei roher 2-(2-Bromophenyl)-3-hydroxypropensäure-methylester (5,95 g) als gelbe Flüssigkeit erhalten wurde, die direkt in der nächsten Stufe verwendet wurde. Der rohe 2-(2-Bromophenyl)-3- hydroxypropensäure-methylester (5,95 g) wurde mit wasserfreiem Kaliumcarbonat (6,38 g) und Dimethylsulfat (2,75 g) in DMF (40 ml) gerührt. Nach 3 h bei Raumtemperatur wurde das Reaktionsgemisch in Wasser geschüttet und mit Ether (2 x 75 ml) extrahiert. Die vereinigten Etherschichten wurden mit Wasser und Kochsalzlösung (1 x) gewaschen und getrocknet- Filtration und Eindampfen ergaben ein gelbes Öl, das beim Stehen kristallisierte, wobei (E)-2-(2-Bromophenyl)-3-methoxypropensäure-methylester (5,20 g, 88 % Ausbeute von ortho-Bromophenylessigsäure-methylester) als kristalliner Feststoff, Fp 68-69ºC, erhalten wurde; IR- Maxima 1712, 1638 cm&supmin;¹; ¹H NMR delta 3,72 (3H,s); 3,86 (3H,s); 7,56 (1H,s) ppm.
  • Kaliumcarbonat (260 mg), (E) -2-(2-Bromophenyl)-3-methoxypropensäure-methylester (250 mg) und Kupfer(I)-chlorid (Katalysator) wurden aufeinanderfolgend zu 3-Methylphenol (210 mg) zugegeben. Das erhaltene Gemisch wurde unter Rühren 3,5 h auf 170ºC erhitzt und dann abkühlen gelassen. Das Gemisch wurde in DMF (3 ml) aufgenommen, dann in Wasser geschüttet, mit verdünnter Salzsäure angesäuert und schließlich mit Ether (3 x 25 ml) extrahiert. Die vereinigten Extrakte wurden sorgfältig mit wäßriger Natriumhydroxid-Lösung (3 x), dann mit Wasser (2 x) und schließlich mit Kochsalzlösung gewaschen und getrocknet. Die erhaltene Lösung wurde konzentriert und chromatographiert (Eluiermittel 30 % Ether in Petrolether), wobei die Titelverbindung (120 mg, 42 % Ausbeute) als weißer kristalliner Feststoff, Fp 79-80 ºC, erhalten wurde; IR-Maxima 1711, 1632 cm&supmin;¹ ; ¹H NMR delta 2,30 (3H,s), 3,62 (3H,s), 3,77 (3H,s), 7,48 (1H,s) ppm.
    • Beispiel 2
  • Dieses Beispiel erläutert die Herstellung von Chlorophenoxy)phenyl]-3-methoxypropensäure-methylester.
  • Natrium (66 mg) wurde in trockenem Methanol (2 ml) unter Stickstoff aufgelöst. 3-Chlorophenol (372 mg) wurde in einer Portion zugegeben, wobei eine gelbe Lösung erhalten wurde, die bei Raumtemperatur 45 min gerührt wurde. Das Methanol wurde abgesampft, wobei ein gelbes Öl erhalten wurde. Dann wurden (E)-2-(2-Bromophenyl)-3-methoxypropensäure-methylester (300 mg, hergestellt wie in Beispiel 1) und eine katalytische Menge Kupferbronze zugegeben. Das erhaltene Gemisch wurde 2 h auf 150ºC und dann 2 h auf 170ºC erhitzt.
  • Eine katalytische Menge Kupfer(I)-chlorid wurde zugesetzt, und das Erhitzen auf 150ºC wurde weitere 2 h fortgesetzt. Analyse des Reaktionsgemischs zu diesem Zeitpunkt durch GC/MS zeigte, daß es aus nichtumgesetztem (E)-2-(2-Bromophenyl)-3-methoxypropensäure-methylester (37 %), 3-(3- Chlorophenoxy)phenol (15 %) und der Titelverbindung (26 %) und auch noch aus einigen kleineren Komponenten (nicht mehr als 5 % des Gemischs) bestand.
    • Beispiel 3
  • Dieses Beispiel erläutert eine alternative Synthese von (E)-3-Methoxy-2-[2-(3-methylphenoxy)phenyl]propensäuremethylester.
  • Ein Gemisch aus ortho-Bromophenylessigsäure-methylester (4,10 g, hergestellt nach der Vorschrift von Beispiel 1) und Selendioxid (4,92 g) wurde 25 h bei 190ºC gerührt. Nach Abkühlung wurde das Gemisch mit Dichloromethan (100 ml) verdünnt und dann durch "Supercel" filtriert. Das Filtrat wurde aufeinanderfolgend mit gesattiger wäßriger Natriumbicarbonat-Lösung (2 x) und Kochsalzlösung gewaschen, dann getrocknet und schließlich konzentriert, wobei eine gelbe Flüssigkeit (3,60 g) erhalten wurde, die (2-Bromobenzoyl)ameisensäure-methylester (52 % gemäß GC-MS) und nichtumgesetzten ortho-Bromophenylessigsäure-methylester enthielt.
  • Kalium-tert-butoxid (2,33 g) wurde zu einer heftig gerührten Suspension von (Methoxymethyl)triphenylphosphononiumchlorid (7,90 g) in Ether (80 ml) bei Raumtemperatur zugegeben. Nach 15 min wurde eine Lösung des rohen (2-Bromobenzoyl)ameisensäure-methylesters (3,60 g) in Ether (10 ml) in einer Portion zugesetzt. Nach weiteren 15 min wurde das Reaktionsgemisch in Wasser (150 ml) geschüttet, worauf die wäßrigen und organischen Schichten getrennt wurden und die erstere mit einer weiteren Portion Ether (100 ml) extrahiert wurde. Die vereinigten Etherschichten wurden aufeinanderfolgend mit Wasser (2 x) und Kochsalzlösung gewaschen, dann getrocknet und schließlich konzentriert, wobei ein gelbes Öl (5,81 g) erhalten wurde, das in einem Verhältnis von ungefähr 6:5 das (E)- und das (Z)-Isomer von 2-(2-Bromophenyl)- 3-methoxypropensäure-methylester enthielt. Chromatographie unter Verwendung von Ether:Hexan (1:1) als Eluiermittel zeigte, daß das reine (Z)-Isomer (0,450 g) als blaßgelbes Öl erhalten worden war; IR-Film 1712, 1638 cm&supmin;¹, ¹H NMR delta 3,71 (3H,s), 3,95 (3H,s), 6,57 (1H,s) ppm.
  • Ein Gemisch aus (Z)-2-(2-Bromophenyl)-3-methoxypropensäuremethylester (0,370 g), 3-Methylphenol (0,294 g), Kaliumcarbonat (0,377 g) und Kupfer(I)-chlorid (katalytische Menge) wurde auf 170ºC erhitzt. Nach 45 min zeigte die Analyse des Gemischs durch GC und Dünnschichtchromatographie, daß es grob genommen gleiche Mengen (E)-2-(2-Bromophenyl)-3-methoxypropensäure-methylester und der Titelverbindung enthielt, wobei nichts von dem ursprünglichen (Z)-2-(2-Bromophenyl)-3-methoxypropensäure-methylester entdeckt werden konnte. Nach weiteren 31/4 h wurde das Reaktionsgemisch abkühlen gelassen. Es wurde in DMF (5 ml) aufgelöst und dann mit Wasser verdünnt, mit verdünnter Salzsäure angesäuert und schließlich mit Ether extrahiert. Diese Extrakte wurden aufeinanderfolgend mit wäßriger Natriumhydroxid-Lösung (3 x), Wasser (2 x) und Kochsalz lösung gewaschen, dann getrocknet, konzentriert und chromatographiert, wobei Ether;Hexan (1:1) als Eluiermittel verwendet wurde. Es wurde die Titelverbindung (0,110 g, 27 % Ausbeute) als nahezu weiser Feststoff erhalten, dessen spektroskopische Daten die gleichen waren als wie bei der Titelverbindung von Beispiel 1.
    • Beispiel 4
  • Dieses Beispiel erläutert die Herstellung von (E)-3-Methoxy-2-[2-(3-[4-phenoxyphenoxy]phenoxy)phenyl]propensäuremethylester.
  • Ein Gemisch aus 3-(4-Phenoxyphenoxy)phenol (4,11 g), (E)- 2-(2-Bromophenyl)-3-methoxypropensäure-methylester (2,0 g, hergestellt nach der Vorschrift von Beispiel 1), Kaliumcarbonat (2,04 g) und Kupfer(I)-chlorid (0,1 g) wurde bei 170 bis 180ºC während 4 h gerührt und dann abkühlen gelassen. Das Gemisch wurde mit Wasser verdünnt und mit Ether extrahiert. Die Etherextrakte wurden aufeinanderfolgend mit wäßriger Natriumhydroxid-Lösung und Kochsalzlösung gewaschen, dann getrocknet und konzentriert, wobei ein brauner Gummi (4,47 g) erhalten wurde. Dieser Gummi wurde unter Verwendung verschiedener Portionen (bis zu 20 %) Ether in Hexan als Eluiermittel chromatographiert, wobei die Titelverbindung (2,06 g, 60 %) als bernsteinfarbener Gummi erhalten wurde.
  • ¹H NMR (90 MHz) delta : 3,62 (3H,s), 3,77 (3H,s), 6,64- 7,49 (17H,m), 7,50 (1H,s) ppm.
    • Beispiel 5
  • Dieses Beispiel erläutert die Herstellung von (E)-3-Methoxy-2-[2-(3-[3-nitrophenoxy]phenoxy)phenyl]propensäuremethylester.
  • Ein Gemisch aus 3-(3-Nitrophenoxy)phenol (1,7 g), (E)-2- (2-Bromophenyl)-3-methoxypropensäure-methylester (2,0 g, hergestellt nach der Vorschrift von Beispiel 1), Kaliumcarbonat (1,0 g) und Kupfer(I)-chlorid (1,0 g) wurde bei 170 bis 180ºC während 5 h gerührt und dann abkühlen gelassen. Das Gemisch wurde mit Wasser verdünnt und mit Ether extrahiert. Die Extrakte wurden aufeinanderfolgend mit wäßriger Natriumhydroxid-Lösung und Kochsalzlösung gewaschen, dann getrocknet und konzentriert, wobei ein braunes Öl (3,12 g) erhalten wurde, Chromatographie unter Verwendung verschiedener Mengen (bis zu 20 % Ether in Hexan als Eluiermittel ergab die Titelverbindung (1,06 g, 34 % Ausbeute) als gelbes Öl.
  • ¹H NMR (270 MHz) delta : 3,60 (3H,s), 3,76 (3H,s), 6,66- 6,83 (3H,m), 7,02 (1H,d) , 7,18 (1H,d), 7,22-7,38 (3H,m), 7,45-7,52 (1H,m), 7,49 (1H,s), 7,78 (1H,m), 7,92-7,97 (1H,m) ppm.

Claims (4)

1. Verfahren zur Herstellung einer Verbindung der allgemeinen Formel (I),
worin die Benzolringe M und N gegebenenfalls einen oder mehrere Substituenten tragen, die unter den Bedingungen des Verfahrens nicht reaktiv sind, bei welchem eine Verbindung der allgemeinen Formel (II),
worin X für Halogen steht, mit einem Phenol der allgemeinen Formel (III) in Gegenwart einer Base oder aber mit einem Salz des Phenols (III) umgesetzt wird, und zwar Vorzugsweise in Gegenwart eines Katalysators, der ein geeignetes Übergangsmetall, ein Übergangsmetallsalz oder eine Übergangsmetallverbindung oder ein Gemisch davon enthält.
2. Verfahren nach Anspruch 1, bei welchem eine katalytische Menge Kupfermetall oder eines Kupfersalzes oder einer Kupferverbindung oder eines Gemischs davon vorliegt.
3. Verfahren nach Anspruch 1 oder 2, welches bei einer Temperatur von 100 bis 200ºC ausgeführt wird.
4. Verfahren nach einem der vorhergehenden Ansprüche, bei welchem die Base aus wasserfreiem Kaliumcarbonat besteht.
DE3887603T 1987-09-09 1988-08-18 Chemisches Verfahren. Expired - Fee Related DE3887603T2 (de)

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