Patent ID: 8853410

Claim:
A process for preparing a compound of the formula (I) wherein R 1 is H, CH 3 , CF 3 , CH 2 CH 3 , CH 2 CF 3 , Cl, or CN; R 2 is H, F, Cl, or CF 3 ; R 3 is H, F, or Cl; R 4 is H, F, Cl, or CF 3 ; R 5 is H, F, Cl or CF 3 ; R 8 is Z-A, wherein Z is CH 2 or CH 2 CH 2 and A is selected from the group consisting of wherein the “#” in the formulae of variables A indicate the bond to Z; and R 9 is H, CH 3 , CH 2 CH 3 , or CH 2 CH 2 CH 3 ; comprising A.3: reacting a compound of the formula (VIII) with a compound of formula (IV) in the presence a chlorinating agent selected from the group consisting of chlorine, sodium hypochlorite, N-chlorosuccinimide and chloramine T, and a base at a temperature from −20 to 120° C. in water or in a solvent selected from the group consisting of cyclic ethers, acyclic ethers, cyclic amides, acyclic amides and aliphatic nitriles, or in mixtures of these solvents, or in mixtures of these solvents and water, to form a compound of formula (XV) wherein R 6 is H; A.4: reacting the compound of the formula (XV) with carbon monoxide and an amine in presence of a palladium catalyst, in which the palladium has an oxidation state of 0 or 2, at a temperature from −20 to 140° C. and a pressure from 0.9 to 100 bar in a solvent selected from the group consisting of aliphatic alcohols having 1 to 4 carbon atoms, aromatic hydrocarbons, cyclic or acyclic ethers, cyclic or acyclic amides, cyclic or acyclic esters, aliphatic nitriles, halogenated hydrocarbons, mixtures of the solvents mentioned above and mixtures of the solvents mentioned above and water to form a compound of formula (I) wherein the compound of formula (VIII) is obtained by A.2: reacting a compound of formula (VII) with a methylenating agent to form a compound of formula (VIII), wherein said methylenating agent is selected from the group consisting of dimethyltitanocene, diphenylmethylphosphine oxide, dimethoxymethylphosphine sulfide, pentamethylphosphonic diamide, dimethyl sulfoxide, (trialkylstannyl)(trimethylsilyl)methane, trimethylsilyl(phenylthio)methane, titanium tetrachloride and diiodomethane or dibromomethane, dichlorotitanocene and aluminum trimethyl, methylenetriphenylphosphine, trimethylsulfonium iodide, dichloro(cyclopentadienyl)zirconium and diiodomethane or dibromomethane dimethyl methanephosphonate, methanesulfonyl chloride, (chloromethyl)trimethylsilylane, diazomethyltrimethyl silane, and Nysted's reagent or a precursor of the methylenating agent selected from freshly powdered triphenylmethyl phosphinium iodide, triphenylmethyl phosphinium bromide and triphenylmethyl phosphinium chloride, at a temperature from −78 to 110° C. in an organic solvent; and the compound of formula (IV) is prepared in a process step B by reacting a compound of formula (II) with formoxime: