Patent ID: 6956129

Claim:
A process for preparing a compound of formula (III) wherein R 1 , R 2 , R 3 and R 4 are identical or different and in each case represent hydrogen, fluorine, chlorine or bromine, at least two of these radicals being other than hydrogen and X represents OR 5 or N(R 6 )(R 7 ), where R 5 represents hydrogen or optionally substituted C 1 -C 10 -alkyl, optionally substituted phenyl or benzyl and R 6 and R 7 are identical or different and in each case represent optionally substituted C 1 -C 10 -alkyl and R 8 represents hydrogen, chlorine, bromine, or optionally substituted C 1 -C 10 -alkyl, the process comprising: reacting (1) an aniline of the formula (VI) wherein R 1 , R 2 , R 3 and R 4 have the meaning indicated in formula (III) with sodium nitrite in aqueous sulfuric acid or sulfuric acid in combination with methanol, or with an alkyl nitrite selected from the group consisting of methyl, ethyl, butyl and amyl nitrite into a diazonium salt and reacting (2) the resulting reaction mixture with a compound of formula (V) wherein X has the meaning indicated in formula (III) and R 8 represents hydrogen, chlorine, bromine or optionally substituted C 1 -C 10 -alkyl, in the presence of a homogeneous, palladium-containing catalyst at a temperature ranging from about −5 to about +100° C.