Patent ID: 7358397

Claim:
A process for preparing compounds of formula (VIII) wherein m is 0, 1, 2 or 3 and n is 1, 2, 3 or 4, where the sum of m+n is a maximum of 4, and R 1 is hydrogen, C 1 -C 12 -alkyl or C 5 -C 15 -arylalkyl and R 2 is in each case independently C 1 -C 12 -fluoroalkyl, C 1 -C 12 -fluoroalkylthio or C 1 -C 12 -fluoroalkoxy; Hal is in each case independently bromine, chlorine or fluorine; and R 4 is 2,4-difluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl or 4-fluoro-3-chloro-phenyl comprising: (1) preparing compounds of formula (I) wherein m is 0, 1, 2 or 3 and n is 1, 2, 3 or 4, m+n is a maximum of 4, and R 1 is hydrogen, C 1 -C 12 -alkyl or C 5 -C 15 -arylalkyl and R 2 is in each case independently C 1 -C 12 -fluoroalkyl, C 1 -C 12 -fluoroalkylthio or C 1 -C 12 -fluoroalkoxy and Hal is each case independently bromine, chlorine or fluorine, by A1) converting a compound of the formula (II) in which is 0, 1, 2 or 3 and R 3 is in each case independently fluorine, chlorine, bromine, iodine, cyano, thiocyanato, hydroxysulphonyl or alkali metal salts thereof, nitro, C 1 -C 12 -alkyl, C 1 -C 12 -fluoroalkyl, C 1 -C 12 -fluoroalkyoxy, C 1 -C 12 -fluoroalkylthio, C 1 -C 12 -alkoxy, C 1 -C 12 -alkoxycarbonyl, di(C 1 -C 12 -alkyl)amino, C 4 -C 14 -aryl or C 5 -C 15 -arylalkyl to a diazonium salt of the formula (III) in which An − is the anion of an acid and A2) reacting the diazonium salt of the formula (III) with compounds of the formula (IV) in which m, n, Hal and R 2 are each as defined under the formula (I) in the presence of a base to give compounds of the formula (V) and B) converting, a compound of the formula (V) with a reducing agent to the compound of the formula (I), in which R 1 is hydrogen, (2) converting at least one compound of formula (I) wherein R 1 is hydrogen, by O-alkylation to a compound of formula (I) in which R 1 is C 1 -C 12 -alkyl or C 5 -C 15 -arylalkyl, and (3) converting at at least one compound of the formula (I) of step (2) by reacting with a compound of the formula (VIIa) or (VIIb) wherein R 4 is 2,4-difluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl or 4-fluoro-3-chlorophenyl and R5 is optionally mono- or poly-chlorine- or -fluorine-substituted phenyl, to the compound of formula (VIII).