Patent ID: 8455689

Claim:
A process for preparing a substituted biphenylanilide of formula (I), wherein X is hydrogen, fluorine or chlorine; R 1 is —NH(CO)R 3 or —N═CR 4 R 5 ; and R 3 , R 4 , R 5 independent from each other represent hydrogen, —C 2 —(C═O)CH 3 , C 1 -C 8 -alkyl, C 1 -C 8 -alkenyl, C 1 -C 8 -alkynyl or C 6 -C 18 -aryl; or R 4 , R 5 together with the carbon atom to which they are attached form a five- or six-membered ring comprising one, two or three hetero atoms selected from the group consisting of N, O, and S; R 2 is cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, C 1 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl, (C 1 -C 6 -alkyl)carbonyl or phenyl; and n is 1, 2 or 3, where in case that n is 2 or 3, the R 2 radicals may also be different, which comprises reacting a compound of formula (II) in which Hal is halogen and X is as defined above, in the presence of a base and a palladium catalyst selected from the group consisting of: a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand, and c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine; in a solvent, with an organoboron compound of formula (III) selected from the group consisting of: (i) a boronic acid of formula (III) wherein m is 2, each Q is a hydroxyl-group, R 2 and n are as defined above, or the anhydrides, dimers or trimers formed thereof; (ii) a boronic acid derivative of formula (III), wherein m is 2, p is 1, each Q is independently selected from the group consisting of F, Cl, Br, I, C 1-4 -alkyl-, C 6-10 -aryl, C 1-4 -alkoxy- and C 6-10 -aryloxy-residues, R 2 and n are as defined above; (iii) a bonnie acid of formula (III), wherein m is 1, p is 2, Q is selected from the group consisting of OH, F, Cl, Br, I, C 1-4 -alkyl-, C 6-10 -aryl-, C 1-4 -alkoxy- and C 6-10 -aryloxy-residues, R 2 and n are as defined above; (iv) a cyclic boronic acid ester of formula (III), wherein m is 2, p is 1, each Q is independently C 1-4 -alkoxy residues which together with the boron atom they are attached form a 5- or 6-membered ring which may be substituted by C 1-4 -alkyl-residues, R 2 and n are as defined above; (v) a boronate of formula (III) wherein m is 3, p is 1, R 2 and n are as defined above; each Q is independently selected from the group consisting of OH, F, Cl, Br, I, C 1-4 -alkyl-, C 6-10 -aryl-, C 1-4 -alkoxy- and C 6-10 -aryloxy-residues, and wherein the negative charge of the boronate anion is compensated by a cation; (vi) a triarylborane of formula (III), wherein m is 0, p is 3, R 2 and n are as defined above; and (vii) a tetraarylborate of formula (III), wherein m is 0, p is 4, R 2 and n are as defined above, and wherein the negative charge of the boronate anion is compensated by a cation; and where the triarylphosphines or trialkylphosphines used may optionally be substituted.