EP1309531A1 - Derives du 4-(trifluoromethyl)-phenol ainsi que de l'ether de 4-(trifluoromethylphenyl)-2-(tetrahydropyranyl) et leur procede de production - Google Patents

Derives du 4-(trifluoromethyl)-phenol ainsi que de l'ether de 4-(trifluoromethylphenyl)-2-(tetrahydropyranyl) et leur procede de production

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Publication number
EP1309531A1
EP1309531A1 EP01962929A EP01962929A EP1309531A1 EP 1309531 A1 EP1309531 A1 EP 1309531A1 EP 01962929 A EP01962929 A EP 01962929A EP 01962929 A EP01962929 A EP 01962929A EP 1309531 A1 EP1309531 A1 EP 1309531A1
Authority
EP
European Patent Office
Prior art keywords
aryl
trifluoromethyl
ether
tetrahydropyranyl
derivatives
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.)
Withdrawn
Application number
EP01962929A
Other languages
German (de)
English (en)
Inventor
Bernd Schäfer
Herve Geneste
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.)
BASF SE
Original Assignee
BASF SE
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
Application filed by BASF SE filed Critical BASF SE
Publication of EP1309531A1 publication Critical patent/EP1309531A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
    • C07F7/0827—Syntheses with formation of a Si-C bond
    • 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
    • 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
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • 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
    • 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
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
    • C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te

Definitions

  • the invention is in the field of derivatives of 4- (trifluoromethyl) phenol and derivatives of 4- (trifluoro-10 methylphenyl) -2- (tetrahydrop ⁇ ranyl) ether and relates to new derivatives and a process for the preparation of these derivatives.
  • WO 98/42664 describes the synthesis of 2-hydroxy-5-trifluoromethylbenzaldehyde by reacting 4- (trifluoromethyl) phenol with tin tetrachloride and paraformaldehyde at 110 ° C. and a reaction time of 12 hours. In addition to the low yield (12%), here too
  • N-formylpiperidine is available from K.K. Laali, G.F. Koser, S. Subramanyam, D.A. Forsyth, J. Org. Chem. 58 (1993) 1385. The yield is only 41%.
  • FR 2735771 describes the synthesis of 2-hydroxy-5-trifluoromethylbenzoic acid from the potassium salt of 4- (trifluoromethyl) phenol via Kolbe synthesis.
  • the reaction requires a reaction temperature of 180 ° C and a carbon dioxide pressure of 10 bar. This requires special equipment. In addition, the yield is only 45%.
  • An alternative preparation is from S. Yamamoto, S. Hashiguchi, S. Miki, Y. Igata, T. Watanabe.
  • EP 206951 AI describes the synthesis of 2-chloro-4- (trifluoromethyl) phenol by trifluoromethylation of 2-chlorophenol
  • J.-C. Blazejewski, R. Dorme, C. Wakselman, J. Chem. Soc, Perkin Trans. 1 (1987) 1861 describe the synthesis of 2-chloro-4- (trifluoromethyl) phenol by reacting 4- (trifluoromethyl) - phenol with N triumchlorite and sulfuric acid. In both cases the yield is less than 10% and the product is with a variety other components contaminated.
  • the direct chlorination of 4- (trifluoromethyl) phenol is described in EP 0188031 B1, DE 2311638 Cl and CH 567359.
  • Simple and quick implementation of the procedure and low demands on the safety devices were desirable. value. In particular, handling toxicologically questionable chemicals should be avoided. A lengthy purification of the product from the reaction mixture should also be avoided. Ideally, it should be possible to use the products directly for further reactions without further purification.
  • a further task was the production of new, previously unknown 2- and 2,5-disubstituted derivatives of 4- (trifluoromethyl) phenol and 2- and 2,5-disubstituted derivatives of 4- (trifluoromethylphenyl) -2- ( tetrahydropyranyl) - ethers.
  • the present invention therefore relates to a process for the preparation of compounds of the general formula (1)
  • R is hydrogen, tetrahydropyran-2-yl
  • Aryl independently of one another represents phenyl, naphthyl, R 1 -C 6 H 4 , characterized in that the compound of formula (2) 4- (trifluoromethylphenyl) -2- (tetrahydropyranyl) ether
  • Essential to the invention is the use of the 4- (trifluoromethylphenyl) -2- (tetrahydropyranyl) ether, it enables targeted derivatization in 2 or in 2 and 5 positions.
  • monosubstituted derivatives are produced.
  • both the symmetrical derivatives (X and Y identical) and the asymmetrical derivatives (X different from Y) can be produced.
  • the preparation of the symmetrical derivatives is particularly preferred.
  • the compound of formula (2) ' 4- (trifluoromethylphenyl) -2- (tetrahydropyranyl) ether is known, it is available synthetically as for example from A. Ouedraogo, J. Lessard, Can. J. Chem. 69 (1991) 474.
  • EX and / or EY compounds are used as electrophiles, in which E represents a good leaving group and X and / or Y inserts the desired side chain.
  • EX CHO
  • the compound of the general formula X-NR 1 2 (3) is suitable as the electrophile EX
  • alkyl radicals for R 1 are branched or unbranched Ci-C ⁇ -alkyl chains, preferably methyl, ethyl, isopropyl, n-propyl, 1-methylethyl, n-butyl, 2-butyl, sec-butyl, tert-butyl, 1- Methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 2-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 2- Hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,
  • alkyl radical R 1 can be localized in the o-, m- and p-positions.
  • Suitable solvents are all solvents which are inert under the reaction conditions.
  • Preferred solvents are tetrahydrofuran (THF), dioxane and Ci-C ⁇ -ether, simple or mixed Ci-C ß- ether, C 4 -C ⁇ 2 hydrocarbons, such as n-butane, isobutane
  • Alkali organyls can be used as bases. It is particularly preferred to use lithium organyl compounds, such as n-butyllithium, sec-butyllithium, t-butyllithium and methyllithium.
  • the process according to the invention includes the knowledge that for the synthesis of the onosubstituted derivatives the base is added in equimolar amounts up to a maximum of 1.8 molar excess. The synthesis of the disubstituted derivatives requires the addition of 2 to 4 equivalents of base.
  • the reaction is carried out in the presence of an amine, in particular a tertiary diamine.
  • amines such as, for example, tetramethylethylenediamine and especially tetraethylethylenediamine diamine and especially tetraethylethylenediamine diamine and especially tetraethylethylenediamine diamine are particularly suitable as suitable amines, such as tetramethylethylene diamine, tetraethylethylene diamine, tetra-n-propylethylene diamine, tetramethylpropylene diamine, tetraethyl-propylene diamine, tetra-n-propylpropylene diamine.
  • the strong base is usually placed in a solvent which is inert under the reaction conditions.
  • the 5 educt 4- (trifluoromethylphenyl) -2- (tetrahydropyranyl) ether which may be dissolved in, for example, tetrahydrofuran or used directly as a melt.
  • the electrophile is then added. This can be in bulk or as a solution. Alternatively, it is possible to present the electrophile and add the lithium organyl. In the synthesis of the disubstituted derivatives, it has proven to be advantageous to submit the base and the ether and then to add the electrophile.
  • the molar ratio of starting material to electrophile depends on the desired compounds and, in the case of the synthesis of the onosubstituted derivatives, is generally between 1: 1 and 1: 1.9; in the case of disubstituted derivatives, usually between 1: 2 and 1: 4.
  • the reaction is carried out at -100 to + 100 ° C, preferably at temperatures between -20 ° C and + 20 ° C.
  • the reaction is carried out in a pressure range from 0.0001 to 200 bar, in particular 0.001 to 20 bar, preferably from 0.001 to 6 bar.
  • the preferred molar ratio of the amine to the lithium organyl is 0: 1 to 30 10: 1, in particular 0: 1 to 5: 1. 0: 1, 1: 1 and 2: 1 are very particularly preferred.
  • the course of the reaction can be determined by detecting the starting material ⁇ 4- (trifluoromethylphenyl) -2- (tetrahydropyranyl) ether in the reaction
  • the 2 and 2,5 -substituted derivatives of 4- (trifluoromethyl) phenol are obtained by splitting off the tetrahydropyranyl group of the corresponding 2 and 2,5-substituted derivatives of 4- (trifluoromethylphenyl) -2- (tetrahydropyranyl) ether , This cleavage is usually carried out under acid catalysis.
  • Carboxylic acids and mineral acids are suitable for acid-catalyzed removal of the tetrahydropyranyl group.
  • Trifluoroacetic acid and hydrochloric acid are particularly preferred.
  • the process according to the invention can be carried out batchwise or continuously, for example using a reaction tube or a stirred reactor cascade.
  • the 2- and 2,5-substituted derivatives of 4- (trifluoromethyl) phenol and 4- (trifluoromethylphenyl) -2- (tetrahydropyranyl) ether produced by the process according to the invention can be used as starting products for the synthesis of dyes, crop protection agents and / or Medicines are used.
  • Another object of the present invention relates to
  • R is hydrogen or tetrahydropyran-2-yl and when R is hydrogen
  • Aryl represents phenyl, R 1 - C 5 H 4 , when R is tetrahydropyran-2-yl
  • R 1 is C 1 -C 8 alkyl
  • Aryl represents phenyl, R ⁇ —C ⁇ EI.
  • the present invention further relates to 2,5-disubstituted derivatives of 4- (trifluoromethyl) phenol and / or 2,5-disubstituted derivatives of 4- (trifluoromethylphenyl) -2- (tetrahydropyranyl) ether of the following formula
  • R is hydrogen, tetrahydropyran-2-yl
  • Y is independent of X for B (OH) 2 , B (OR 1 ), B (OAryl) 2 ,
  • R 1 independently of one another for Ci-Cs-alkyl
  • Aryl independently of one another represents phenyl, naphthyl, R 1 -CgH 4 ,
  • a cloudy solution is formed, which is added dropwise after 15 min to 750 ml of 38% hydrochloric acid in 500 ml of water within 30 min at a maximum of 45 ° C. There is a strong gas development.
  • the mixture is stirred overnight, the aqueous phase is separated off, 70 ml of M 5 dioxane / HCl solution are added to the organic phase and the mixture is stirred again overnight.
  • the product is crystallized by cooling to -30 ° C (2 to 3 h), suction filtered, washed with 500 ml of cold pentane and that Product air-dried. 220 g (GC: 98.3%, 1.13 mol, yield 75%) of 2-hydroxy-5- (trifluoromethyl) benzaldehyde are obtained in the form of colorless crystals (mp: 60.1 to 61.8 ° C.).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un procédé de production de dévirés du 4-(trifluorométhyl)-phénol et de l'éther 4-(2-trifluorométhyl)-phényl)-2-tétrahydropyranyl) substitués en 2 et 2,5 ainsi que de nouveaux dérivés. Le procédé est caractérisé en ce que l'on fait réagir, en présence d'une base, le composé de la formule éther de (2) 4-(trifluorométhylphényl)-2-(tétrahydropyranyl) avec un électrophile E-X ou une combinaison d'électrophiles E-X et E-Y, X et Y ayant la signification donnée dans la description.
EP01962929A 2000-08-11 2001-08-09 Derives du 4-(trifluoromethyl)-phenol ainsi que de l'ether de 4-(trifluoromethylphenyl)-2-(tetrahydropyranyl) et leur procede de production Withdrawn EP1309531A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10040051A DE10040051A1 (de) 2000-08-11 2000-08-11 Derivate des 4-(Trifluormethyl)-phenols sowie Derivate des 4-(Trifluormethylphenyl)-2-(tetrahydropyranyl)ethers und Verfahren zu ihre Herstellung
DE10040051 2000-08-11
PCT/EP2001/009222 WO2002014250A1 (fr) 2000-08-11 2001-08-09 Derives du 4-(trifluoromethyl)-phenol ainsi que de l'ether de 4-(trifluoromethylphenyl)-2-(tetrahydropyranyl) et leur procede de production

Publications (1)

Publication Number Publication Date
EP1309531A1 true EP1309531A1 (fr) 2003-05-14

Family

ID=7652635

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01962929A Withdrawn EP1309531A1 (fr) 2000-08-11 2001-08-09 Derives du 4-(trifluoromethyl)-phenol ainsi que de l'ether de 4-(trifluoromethylphenyl)-2-(tetrahydropyranyl) et leur procede de production

Country Status (8)

Country Link
US (1) US20040092754A1 (fr)
EP (1) EP1309531A1 (fr)
JP (1) JP2004506033A (fr)
AR (1) AR031259A1 (fr)
AU (1) AU2001284001A1 (fr)
CA (1) CA2418749A1 (fr)
DE (1) DE10040051A1 (fr)
WO (1) WO2002014250A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040204422A1 (en) 2003-04-14 2004-10-14 Abbott Gmbh & Co. Kg. N-[(Piperazinyl)hetaryl]arylsulfonamide compounds
US7858666B2 (en) 2007-06-08 2010-12-28 Mannkind Corporation IRE-1α inhibitors
WO2020023438A2 (fr) 2018-07-23 2020-01-30 Celgene Quanticel Research, Inc. Méthode de préparation d'un inhibiteur de bromodomaine

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2016624A1 (de) * 1970-04-08 1971-10-21 Farbenfabriken Bayer Ag, 5090 Leverkusen Mikrobizide Mittel
US3928416A (en) * 1972-03-14 1975-12-23 Rohm & Haas Herbicidal 4-trifluoromethyl-4{40 nitrodiphenyl ethers
DE2407148A1 (de) * 1974-02-15 1975-08-28 Bayer Ag Mittel zur regulierung des pflanzenwachstums
US4321084A (en) * 1977-09-23 1982-03-23 Stauffer Chemical Company Certain halogenated phenols as antidotes for thiocarbamate herbicides
DE3037414A1 (de) * 1980-10-03 1982-05-19 Basf Ag, 6700 Ludwigshafen 4-trifluormethylphenyl-(di)thiophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen
FR2547811B1 (fr) * 1983-06-23 1985-10-31 Rhone Poulenc Spec Chim Procede de chloration de derives aromatiques
US4548640A (en) * 1983-10-21 1985-10-22 Fmc Corporation Allylthiodiphenyl ether herbicides
US5739135A (en) * 1993-09-03 1998-04-14 Bristol-Myers Squibb Company Inhibitors of microsomal triglyceride transfer protein and method
ES2087019B1 (es) * 1994-02-08 1997-03-16 Bobel246 S L Uso de derivados de fenoles 2,4-disubstituidos como inhibidores de la 5-lipoxigenasa.
WO1997049710A1 (fr) * 1996-06-21 1997-12-31 Merck Sharp & Dohme Limited Derives spiro-piperidine et leur utilisation comme agents therapeutiques
US6410664B1 (en) * 1997-03-24 2002-06-25 Cryovac, Inc. Catalyst compositions and processes for olefin polymers and copolymers

Non-Patent Citations (1)

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Title
See references of WO0214250A1 *

Also Published As

Publication number Publication date
WO2002014250A1 (fr) 2002-02-21
US20040092754A1 (en) 2004-05-13
AR031259A1 (es) 2003-09-17
DE10040051A1 (de) 2002-02-21
AU2001284001A1 (en) 2002-02-25
JP2004506033A (ja) 2004-02-26
CA2418749A1 (fr) 2003-02-10

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