Patent ID: 6066766
Filing Date: 2000-05-23
Classification: C07C

Abstract:
A process for the preparation of 4-chlorobiphenyls of the formula (I) ##STR6## in which R.sub.1 a to R.sub.4 a are identical or different and have the meaning hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl, C.sub.2 -C.sub.12 -alkynyl, C.sub.1 -C.sub.12 -alkoxy, C.sub.1 -C.sub.12 -acyloxy, O-phenyl, O-benzyl, aryl, heteroaryl, F, Cl, NO.sub.2, CN, SO.sub.2 R, SOR, NH(C.sub.1 -C.sub.6 -alkyl), N(C.sub.1 -C.sub.6 -alkyl).sub.2, C.dbd.N(C.sub.1 -C.sub.6 -alkyl), CX.sub.3, COO--(C.sub.1 -C.sub.12 -alkyl), CO--(C.sub.1 -C.sub.12 -alkyl), CO-phenyl, COO-phenyl, CON(C.sub.1 -C.sub.8 -alkyl).sub.2, CONH(C.sub.1 -C.sub.8 -alkyl), CHCHCOO--(C.sub.1 -C.sub.12 -alkyl), N(Si(C.sub.1 -C.sub.4 -alkyl).sub.3), PO(phenyl).sub.2, PO--(C.sub.1 -C.sub.8 -alkyl).sub.2 or PO.sub.3 --(C.sub.1 -C.sub.8 -alkyl).sub.2, where R is aryl, F or C.sub.n F.sub.2n+1 where n=1 to 12, and where X is F, Cl or Br; and R.sub.5 a to R.sub.9 a are identical or different and have the meaning hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl, C.sub.2 -C.sub.12 -alkynyl, C.sub.1 -C.sub.12 -alkoxy, O-phenyl, O-benzyl, aryl, heteroaryl, F, Cl, NO.sub.2, CN, SO.sub.2 R, SOR, where R is aryl, which comprises reacting a haloaromatic of the formula (II) ##STR7## with an aryl Grignard compound of the formula (III) ##STR8## in which Hal is chlorine, bromine or iodine, in the presence of a palladium catalyst of the formula (IV) ##STR9## in which R.sub.1 to R.sub.8 are identical or different and are hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.5 -C.sub.8)-cycloalkyl, (C.sub.1 -C.sub.4)-alkoxy, fluorine, NH.sub.2, NH--(C.sub.1 -C.sub.4 -alkyl), N(C.sub.1 -C.sub.4 -alkyl).sub.2, CO.sub.2 -alkyl-(C.sub.1 -C.sub.4) or phenyl, or R.sub.1 and R.sub.2, or R.sub.2 and R.sub.3, or R.sub.3 and R.sub.4 ; and optionally R.sub.5 and R.sub.6, or R.sub.6 and R.sub.7, or R.sub.7 and R.sub.8 together form an aliphatic or aromatic ring, R.sub.9 to R.sub.12 are identical or different and are C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl or aryl which is optionally substituted by 1 to 3 substituents selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy and halogen, and Y is an anion of an organic or inorganic acid.