Method for producing unsymmetrically substituted biphenyls

Details Method for producing unsymmetrically substituted biphenyls Method for producing unsymmetrically substituted biphenyls

C - Chemistry, Metallurgy

07

C

C07C 255/50 (2006.01) C07C 253/30 (2006.01) C07C 255/54 (2006.01)

Patent

CA 2246354

A method for the synthesis of unsymmetrically substituted biphenyls of general formula (I) where R = H, alkyl, alkoxy, F, Cl or 4-phenylmethoxy comprises the palladium-catalysed coupling of an aryl Grignard compound of the general formula (II) (where R = H, alkyl, alkoxy, F, Cl or 4-phenylmethoxy; X = Cl, Br or I), in which the ring bearing substituent R may also have further substituents, with bromobenzonitrile (which may bear further substituents), at 10-100 ~C, the Grignard compound being added slowly over a period of at least 30 minutes. The palladium catalyst is added at a concentration of 0.1 to 20.0 % molar based on the benzonitrile.

On décrit un procédé de synthèse de diphényles à substitution asymétrique, de la formule générale (I) dans laquelle R représente H, alkyle, alcoxy, F, Cl ou 4-phénylméthoxy, lequel procédé consiste à coupler, au moyen d'un catalyseur au palladium, un composé aryle Grignard de la formule générale (II) (dans laquelle R représente H, alkyle, alcoxy, F, Cl ou 4-phénylméthoxy et X représente Cl, Br ou I, le noyau portant le substituant R pouvant comporter également d'autres substituants), avec du bromobenzonitrile (lequel peut comporter d'autres substituants), à une température de l'ordre de 10 à 100 ·C, le composé Grignard étant ajouté lentement, sur une période d'au moins 30 minutes. On ajoute le catalyseur au palladium selon une concentration en pourcentage molaire de l'ordre de 0,1 à 20,0 par rapport au benzonitrile.

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