Process for the preparation of thioether-substituted aromatic ke

Details Process for the preparation of thioether-substituted aromatic ke Process for the preparation of thioether-substituted aromatic ke

1998-06-02

2000-08-08

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfur containing

568 43, C07C31900

Patent

active

061004316

ABSTRACT:
The preparation of aromatic ketones substituted with a thioether group at the ortho position is accomplished by the initial reaction of an aromatic nucleus substituted with a halide and an ortho nitro group with a nitroalkane in the presence of a hydroxide base. The resulting ortho-nitroalkyl nitroarene compound is converted to the corresponding ortho-nitroaryl ketone by an oxidative Nef reaction. The aromatic nitro group of the ortho-nitroaryl ketone is replaced with a thioether group by reaction with a thiolate anion, most preferably under phase-transfer conditions. Aromatic ketones may be used to prepare various pharmaceutical and herbicidal compounds.

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