Abstract:
The present invention relates to novel processes for the production of compounds of formula (I) wherein Hal and Hal′ are independently selected from Cl and F, and R1 is selected from Cl, F and H.
Abstract:
A process for producing compounds of formula (VIIa) and (VIIb) wherein X is a leaving group; Y and Y1 are idependently Cl or Br; and Z is Cl, Br or a haloalkyl group which process comprises a) reacting a compound of formula (VII) wherein X, Y, Y1 and Z are as defined for compounds (VIIa) and (VIIb) with a substantially optically pure chiral amine in a solvent to form a diastereoisomeric salt; b) separating the diastereomeric salt of each enantiomer; c) converting the diastereomeric salt of each anantiomer separately to compounds of formulae (VIIa) and (VIIb) respectively by acid or base hydrolysis, the use of the compounds in making pyrethroid insecticides and novel intermediates.
Abstract:
The present invention relates to novel processes for the production of compounds of formula (I) wherein Hal and Hal′ are independently Cl or F, and R1 is H, Cl or F.
Abstract:
A process for the preparation of gamma-cyahlothrin comprising a) chlorinating 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid to give 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride; b) esterifying 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride with 3-phenoxy benzaldehyde in the presence of a source of cyanide to form a diastereoisomeric mixture of cyhalothrin isomers and c) epimerising the diastereoisomeric mixture under conditions in which the least soluble diastereoisomer crystallises from solution.
Abstract:
A process for the purification of a compound of general formula I: wherein: R1 is hydrogen or C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl (any of which may optionally be substituted with one or more substituents selected from halogen and OH) or COOR4, COR6, CONR4R5 or CONHSO2R4; R4 and R5 are each independently hydrogen or C1-C4 alkyl optionally substituted with one or more halogen atoms; R6 is a halogen atom or a group R4; R2 is hydrogen or halo; R3 is C1-C4 alkyl, C2-C4 alkenyl or C2-C4 alkynyl, any of which may optionally be substituted with one or more halogen atoms, or halo; or, where appropriate, a salt thereof; from a mixture containing the compound of general formula I together with one or more isomers or di-nitrated analogues thereof; the process comprising dissolving the mixture in a suitable crystallisation solvent and recrystallising the product from the resulting crystallisation solution; characterised in that the crystallisation solution contains not more than 25% loading of the compound of general formula I wherein loading is defined as: weight of pure compound of formula I × 100 weight of pure compound of formula I + weight of solvent and in that the temperature to which the solution is cooled for crystallisation is not greater than about 30° C.
Abstract translation:用于纯化通式I化合物的方法:其中:R 1是氢或C 1 -C 6烷基,C 2 -C 6烯基或C 2 -C 6炔基(其中任何一个可以任选地被一个或多个选自卤素和 OH)或COOR 4,COR 6,CONR 4 R 5或CONHSO 2 R 4; R 4和R 5各自独立地为氢或任选被一个或多个卤素原子取代的C 1 -C 4烷基; R 6为卤素原子或基团R 4; R 2为氢或卤素; R 3为 C 1 -C 4烷基,C 2 -C 4烯基或C 2 -C 4炔基,其中任何一个可任选被一个或多个卤素原子或卤素取代; 或其合适的盐,由含有通式Ⅰ化合物的混合物与一种或多种异构体或其二硝化类似物组成; 该方法包括将混合物溶解在合适的结晶溶剂中并从所得结晶溶液中重结晶产物;其特征在于结晶溶液含有不超过25%的通式I化合物的负载,其中负载定义为: 溶液冷却至结晶的温度不大于约30℃
Abstract:
A process for the preparation of gamma-cyhalothrin comprising steps of a) chlorinating 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid to give 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride and b) esterifying 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride with the (S)-cyanohydrin of 3-phenoxy benzaldehyde (III).
Abstract:
A process for the purification of a compound of general formula I: ##STR1## wherein R.sup.1 is hydrogen or C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl, any of which may optionally be substituted with one or more substituents selected from halogen and hydroxy; or COOR.sup.4, COR.sup.6, CONR.sup.4 R.sup.5 or CONHSO.sub.2 R.sup.4 ;R.sup.4 and R.sup.5 independently represent hydrogen or C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen atoms;R.sup.6 is a halogen atom or a group R.sup.4 ;R.sup.2 is hydrogen or halo; andR.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl, any of which may optionally be substituted with one or more halogen atoms; or halo; or, where appropriate, a salt thereof;from a mixture containing the compound of general formula I together with one or more isomers or di-nitrated analogs thereof; the process comprising dissolving the mixture in a suitable crystallization solvent and recrystallizing the product from the resulting crystallization solution wherein the crystallization solution contains not more than 25% loading of the compound of general formula I, loading being defined as: ##EQU1## and wherein the temperature to which the solution is cooled for crystallization is not greater than about 30.degree. C.; wherein, after the addition of the crystallizing solvent but before recrystallization, the crystallization solution is subjected to at least one wash with an aqueous solution having an acid pH. The process is particularly useful for purifying acifluorfen produced via a route starting with m-cresol.
Abstract:
The present invention relates to novel processes for the production of compounds of formula (I) wherein Hal and Hal′ are independently selected from Cl and F, and R1 is selected from Cl, F and H.
Abstract:
A process for producing fomesafen from acifluorfen comprises the steps of (a) converting acifluorfen to its acid chloride, (b) coupling the acid chloride so formed with methanesulphonamide to form crude fomesafen and (c) purifying the crude fomesafen, characterized in that each of the steps is carried out in a single common solvent, which is preferably a chloroalkane. Preferably the steps are telescoped together so that there is no isolation of the product for any step until fomesafen is obtained.
Abstract:
A process for the purification of a compound of general formula I: ##STR1## wherein R.sup.1 is hydrogen or C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl, any of which may optionally be substituted with one or more substituents selected from halogen and hydroxy; or COOR.sup.4, COR.sup.6, CONR.sup.4 R.sup.5 or CONHSO.sub.2 R.sup.4 ;R.sup.4 and R.sup.5 independently represent hydrogen or C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen atoms;R.sup.6 is a halogen atom or a group R.sup.4 ;R.sup.2 is hydrogen or halo; andR.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl, any of which may optionally be substituted with one or more halogen atoms; or halo;or, where appropriate, a salt thereof;from a mixture containing the compound of general formula I together with one or more isomers or di-nitrated analogues thereof; the process comprising dissolving the mixture in a suitable crystallisation solvent and recrystallising the product from the resulting crystallisation solution wherein the crystallisation solution contains not more than 25% loading of the compound of general formula I, loading being defined as: ##EQU1## and wherein the temperature to which the solution is cooled for crystallisation is not greater than about 30.degree. C.; wherein, after the addition of the crystallising solvent but before recrystallisation, the crystallisation solution is subjected to at least one wash with an aqueous solution having an acid pH followed by back extraction with fresh crystallising solvent. The process is particularly useful for purifying acifluorfen produced via a route starting with m-cresol.