US 3,946,072 AGranted

Method for reacting organic halides

AssigneeThe University of Akron

InventorsMichael F. Farona, James F. White

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Abstract

A method for carrying out reactions of the Friedel-Crafts type, such as alkylation, acylation, polymerization, sulfonylation and dehydrohalogenation. The reactions are catalyzed by arene-metal tricarbonyl complexes and when the reaction vessel contains aromatic substrates the catalyst may be generated in situ from a metallic hexacarbonyl. The arene-metal tricarbonyl catalyst is more selective than conventionally employed Friedel-Craft catalysts in that it yields generally para isomers with little of the ortho variety and very little if any of the meta variety when the aromatic substrate is reacted with organic halide. It is also possible to form the arene-metal tricarbonyl catalyst outside of the reaction vessel and then proceed by adding it to the vessel containing the substrate and the organic halide as is the case with dehydrohalogenation reactions wherein there are no aromatic rings available, the substrate in that instance being aliphatic.

Claims8

Dependent claims

The process of reacting an organic halide with an aromatic substrate to form an aromatic product comprising the steps of:

charging a reaction vessel with a metallic hexacarbonyl compound having the general formula M(CO).sub.6 wherein M is selected from the group consisting of Cr, Mo and W, adding an aromatic substrate having the general formula ##SPC9##
wherein R' is selected from the group consisting of hydrogen and sulfonyl chloride with the proviso that at least one of said R' is other than hydrogen, reacting said metallic hexacarbonyl compound with part of said aromatic substrate to yield an arene metal tricarbonyl catalyst having the general formula ##SPC10##
charging the reaction vessel with an organic halide having the general formula RX wherein R is an alkyl group having from 1 to about 20 carbon atoms, and X is selected from the group consisting of bromine, chloride and fluorine, heating said reaction vessel from ambient temperatures to a temperature sufficient to cause said catalyst to remove the halide from said organic halide with generation of a carbonium ion from said organic halide so that said carbonium ion will attack the remaining part of said aromatic substrate to yield the aromatic product.

Dependencies are inferred from the claim text.

Facts

Application: 05/459,485Filed 10 Apr 1974 · division
Priority: 1 Mar 1971
Granted: 23 Mar 1976
Term ends: Not estimatedThe source records don’t support an estimate.

Classification23 codes

B01J 31/2295
Unsaturated compounds used as ligands: cyclic compounds, e.g. cyclopentadienyls
B01J 31/20
Containing coordination complexes: carbonyls
C07C 2/861
By condensation between a hydrocarbon and a non-hydrocarbon: the non-hydrocarbon contains only halogen as hetero-atoms
C07C 37/18
By reactions increasing the number of carbon atoms: by condensation involving halogen atoms of halogenated compounds