Monoorganylation of dihaloaromatics

A method for making compounds of the formula:

• ##STR8## comprising reacting a compound of the formula:
• ##STR9## with the compound RMX' wherein:
• ##STR10## is an aromatic moiety selected from one of benzene, naphthalene or anthracene;
• X is individually Cl or Br, there being no more than one Br atom in the starting compound;
• Y is hydrogen, C.sub.1 to C.sub.20 branched or straight chain alkyl or alkoxy, cycloalkyl, alkaryl, aryl, aralkyl, substituted alkyl, cycloalkyl, alkaryl, aryl, aralkyl, in which the substituents do not react with RMX';
• R is C.sub.1 to C.sub.20 branched or straight chain alkyl containing no tertiary carbon centers, cycloalkyl, alkaryl, aralkyl, or aryl;
• M is Mg or Zn;
• and
• X' is Cl, Br, or I;
• in the presence of a nickel/bidentate phosphorus catalyst complex or a nickel/tridentate phosphorous catalyst complex;
• wherein the bidentate phosphorous ligands are selected from the group consisting of:
• (C.sub.6 H.sub.5).sub.2 P(CH.sub.2).sub.a P(C.sub.6 H.sub.5).sub.2, where a=1, 2, 3 or 4;
• (CH.sub.3).sub.2 P(CH.sub.2).sub.b P(CH.sub.3).sub.2, where b=1, 2, 3 or 4;
• and
• cis-(C.sub.6 H.sub.5).sub.2 PCH=CHP(C.sub.6 H.sub.5).sub.2 ;
• and the tridentate ligands are selected from the group consisting of:
• [(C.sub.6 H.sub.5).sub.2 P].sub.3, CH,
• [(C.sub.6 H.sub.5).sub.2 PCH.sub.2 ].sub.3 CCH.sub.3,
• [(C.sub.2 H.sub.5).sub.2 PCH.sub.2 ].sub.3 CCH.sub.3,
• [o-(C.sub.6 H).sub.5 PC.sub.6 H.sub.4 ].sub.2 PC.sub.6 H.sub.5,
• [o-(C.sub.2 H.sub.5).sub.2 PC.sub.6 H.sub.4 ].sub.2 PC.sub.6 H.sub.5,
• C.sub.6 H.sub.5 P[(CH.sub.2).sub.2 P(cyclohexyl).sub.2 ].sub.2,
• [(C.sub.6 H.sub.5).sub.2 P(CH.sub.2).sub.2 ].sub.2 PC.sub.6 H.sub.5,
• C.sub.6 H.sub.5 P[(CH.sub.2).sub.2 P(CH.sub.3).sub.2 ].sub.2,
• CH.sub.3 P[(CH.sub.2).sub.2 P(CH.sub.3).sub.2 ].sub.2,
• CH.sub.3 P[(CH.sub.2).sub.2 P(C.sub.6 H.sub.5).sub.2 ].sub.2,
• (CH.sub.3).sub.2 P(CH.sub.2).sub.2 P(C.sub.6 H.sub.5)(CH.sub.2).sub.2 P(C.sub.6 H.sub.5).sub.2,
• (CH.sub.3).sub.3 CCH.sub.2 P[(CH.sub.2).sub.2 P(CH.sub.3 C(CH.sub.3).sub.3).sub.2 ].sub.2,
• and ##STR11## with the nickel/bidentate phosphorus catalyst complex, at least one molar equivalent, based on nickel, or triarylphosphine is also present during the reaction.