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Trihalomethylpyridine Compounds

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Trihalomethylpyridine Compounds Patentamt JEuropaisches ® Publication number: 0 1 07 866 9 European Patent Office B 1 Office europeen des brevets © EUROPEAN PATENT SPECIFICATION (§) Dateof publication of patent specification: 30.03.88 © Int. CI.4: C 07 D 213/61 ^) Application number: 83110864.2 (22) Date of filing: 26.07.78 (§j) Publication number of the earlier application in accordance with Art. 76 EPC: 0 021 453 (§) Trihalomethylpyridine compounds. INDUSTRIES (§) Priority: 12.08.77 GB 3403977 ® Proprietor: IMPERIAL CHEMICAL 26.10.77 GB 4454177 PLC 09 02 78 GB 523078 Imperial Chemical House Millbank London SW1P3JF(GB) (43) Dateof publication of application: 09.05.84 Bulletin 84/19 ® Inventor: Cartwnght, David 1 Stonehaven Drive Woodley Reading Berkshire (GB) (45) Publication of the grant of the patent: 30.03.88 Bulletin 88/13 _ (74) Representative: Houghton, Malcolm... , John, .. et al@ Imperial Chemical Industries ® Designated Contracting States: PLC Legal Department: Patents PO Box 6 BE CH DE FR GB LU NL SE Welwyn Garden City Herts, AL7 1 HD (GB) (58) References cited: (58)^ References cited: EP-A-0 000483 DE-A-2 223 894 EP-A-0 002 800 DE-A-2 812 571 EP-A-0 009 212 DE-A-2 812 607 BE-A- 857 022 DK-A- 326 078 BE-A-862325 FR-A-2236 861 CH-D- 947 176 278 675 FR-A-2288 089 FR-A-2406 629 The file contains technical information FR-A-2 406 630 submitted after the application was filed and GB-A-1 421 619 not included in this specification GB-A-1 424 359 Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1 ) European patent convention). Courier Press, Leamington Spa, England. ) 107 866 i) References cited: GB-A-2 045 245 US-A-2 516402 US-A-2 679 453 US-A-3244 722 US-A-3 244 722 US-A-3412095 US-A-3418 323 US-A-3 420 833 US-A-3461 125 US-A-3 732 230 US-A-4205175 US-A-4309 548 US-A-4317 913 HELVETICA CHIMICA ACTA, vol. 59, f asc. 1 , no. 23-24, 1976, pages 229-230 F. MUTTERER et al.: Halogenierte Pyridine V. Fluorierte und bromierte Pyridinverbindungen" Wc Bee et al, Ind. Eng. Chem; 1947, 39, 389 Vlalthes et al (Angew. Chem. Internat. Edit., 1963,2, 144 =ritz et al., Helvetica Chimica Acta, 1976, 59, 179-190 =laatsch J. Org. Chem., 27, 1406, 1962 107 bbb Description divided This application is divided from Application No. 80103907.4 (EP— A— 0 021 453) which is itself from Application No. 78300203.3 (EP— A— 0 001 473). The present invention relates to a process for preparing certain trihalomethylpyndine compounds useful in the preparation of compounds having herbicidal properties, and to the novel compounds, 2,3- dichloro-5-trichloromethylpyridine and 2,3-dichloro-5-trifluoromethylpyridine. According to the present invention there is provided a process for preparing a compound of formula (II) 3 5 wherein X is chlorine or fluorine, Y is hydrogen or cnionne ana c. is imiuuiumeu.yi «. difluoromethyl, characterised by fluorinating a compound of formula (II') o vherein Y is hydrogen or chlorine. The invention also includes the novel compound, 2,3-dichloro-5-trichloromethylpyndine to and the novel compound, 2,3-dichloro-b-tritiuorometnyipyriaine States Patent The compound 2,3-dichloro-5-trichloromethylpyridine is mentioned by name in United Specification No. 3,244,722 but no method is disclosed by which it can be prepared. the formula The compounds of formula (II) are useful in the preparation of herbicidal compounds of (I) 40 ^0_^J_0-CH-R2 45 wherein Z is trifluoromethyl or chlorodifluoromethyl; Y is hydrogen or chlorine; n is nyorogen or h_4 alkyl; and R2 is cyano; carboxy; carboxamido of formula — CNR3R4 II 50 O wherein R3 is hydrogen or alkyl and R4 is hydrogen, optionally nyaroxy- or pnenyi-suubiuuwu 0,-4 a *y , R is or C, alkyl, phenyl or chlorophenyl, Cw alkoxy or a group of formula NRSR6 wherein hydrogen f NR3R4 constitutes pyrrolidine, pipendmo, or 55 and R6 is hydrogen, C,-4 alkyl, phenyl or chlorophenyl, or — morpholino; a group of formula — CSR7 bears wherein R7 is alkyl or phenyl; alkoxycarbonyl optionally substituted with hydroxy, alkoxy, halogen or a groupnrnun ofnf formula (I)(li wherein KR2 is — C— 0— ; 65 0 107 866 a group of formula — C(0CH2CH2)„0R8 II 0 5 wherein R8 is a C,_4 alkyl and n is an integer of 1 to 5; optionally halo- or methyl-substituted cyclohexyioxy- carbonyl; (C3_6 alkenyloxy)carbonyl; optionally halo- or methyl-substituted phenoxycarbonyl; or benzyloxycarbonyl, the phenyl group of which being optionally substituted with halogen or methyl; or, in the case of compounds wherein R2 is carboxy, salts thereof. When R3 is alkyl it is preferably d-,2 alkyl, for example alkyl. w When R7 is alkyl it is preferably Ci-Z0 alkyi, especially C,-^ alkyl, for example methyl, ethyl, propyl, butyl and dodecyl. When R2 is alkoxycarbonyl, it is preferably {C,^ alkoxy)carbonyl especially (Cn_12 alkoxy)carbonyl and particularly (C-,_8 alkoxy)carbonyl; for example the alkoxy moiety may be methoxy, ethoxy, propoxy, butoxy, /sobutoxy, secbutoxy, and octyloxy. is Salts of those compounds wherein R2 is carboxy may be prepared by conventional methods known for the preparation of salts of carboxylic acids. Typical salts include metal salts and ammonium salts. Metal salts include salts formed with alkali metal cations, for example sodium, potassium and lithium, and alkaline earth metal cations, for example calcium, strontium and magnesium. Ammonium salts include salts formed with the ammonium cation or with a mono-, di-, tri, or tetra-substituted ammonium cation in 20 which the substituents may be, for example, C-,-6 aliphatic radicals, for example, C-,-6 alkyl. One group of compounds includes those in which the group Z is CF3, Y is hydrogen, R1 is methyl, and R2 is as defined above. Within this group, R2 may be, for example, carboxy either as such or in the form of a salt thereof, or may be alkoxycarbonyl, for example, Ci-e alkoxycarbonyl. 25 Another group of compounds includes those in which the group Z is CF3, Y is chlorine, R1 is methyl and R2 is as defined above. Within this group, R2 may be, for example, carboxyl either as such or in the form of a salt thereof, or may be alkoxycarbonyl, for example C-,-6 alkoxycarbonyl. A further group of compounds includes those in which the group Z is chlorodifluoromethyl, R1 is a methyl group, and R2 is as defined above. Within this group of compounds, R2 may be, for example, 30 carboxy either as such or in the form of a salt thereof, or may be alkoxycarbonyl, for example C,-6 alkoxycarbonyl. These herbicidal pyridine compounds are among the compounds described in European Patent Application No. 78300203.3 (Publication No. 001,473) wherein herbicidal processes and compositions utilising the compounds are described. 35 Three general routes (described below as Routes, A, B and C) are available for the preparation of the herbicidal pyridine compounds from compounds of the formula (II) 10 wherein X, Y and Z are as defined above. 45 50 55 60 4 0 107 866 toute A is outlined in the following scheme. Route A OCH„ � o (II) \ '5 ^N� ft~^> 20 r O — V___7 — 3 (in 25 z Y Demethylating agent ^Y^^y^ ( III ) e.g. Pyridine — • — un ^ j 30 hydrochloride IV) 35 1 R i <>> lV) ^ Hal-CH-R2 40 V) i-iai is In Route A, the symbols R , Rz, X, Y and Z have the meanings previously assigned to tnem, 45 halogen, preferably chlorine or bromine, and M is a cation, for example sodium. In Route A, the suitably substituted halogeno pyridine (II) is reacted with a metal salt of p- methoxyphenol. The reaction is preferably carried out in a solvent or diluent, for example methyl ethyl ketone, tetrahydrofuran, dimethylsulphoxide or dimethylacetamide. The 2-p-methoxyphenoxy compound (III) so obtained is then demethylated by a standard procedure, for example by heating with pyridine so hydrochloride or with hydrogen bromide in acetic acid, to obtain the corresponding p-hydroxy compound the sodium potassium salt) with the (IV) . This in turn is reacted in the form of its metal salt (for example or appropriate halogeno-alkanoic acid derivative (V) to obtain the required compound (I). Preferably this reaction is carried out in a solvent or diluent, for example methyl ethyl ketone. 55 Route B is outlined in the following scheme:— (||) + HO 0H Base^ (IV) 60 R 65 (IV) + Hal-CH-R Base (I; o 9 107 866 According to Route B, the appropriately substituted 2-halogenopyridme (II) is reacted with hydroquinone in the presence of a base to give the p-hydroxyphenoxy compound (IV) already referred to in Route A. The reaction is preferably carried out in a solvent or diluent for the reactants. Examples of suitable solvents include aprotic solvents, for example dimethylformamide. The reaction is preferably accelerated 5 by heating, for example to a temperature in the range from 50 to 150°. The base used in the reaction may be, for example, an inorganic base, for example sodium or potassium carbonate. The second stage of route B is identical with the last stage of Route A and requires no further description. 'O Route C '5 3ase^ (I) (VI) 20 According to Route C, the appropriately substituted 2-halogenopyridine (II) is reacted with a 2-{p- hydroxyphenoxy)propionic acid derivative (VI) in the presence of a base, giving the compound of the invention (I) directly.
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