Process for the preparation of bromoarylacetylene and aryldiacet

Details Process for the preparation of bromoarylacetylene and aryldiacet Process for the preparation of bromoarylacetylene and aryldiacet

1978-12-07

1980-09-16

Morgenstern, Norman

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

Organic compounds

Oxygen containing

568807, 568809, 568813, C07C 2900, C07C 3310, C07C 3304

Patent

active

042231728

ABSTRACT:
Bromoarylacetylenes such as m-bromophenylacetylene and certain precursors to such bromoarylacetylene are prepared by reacting an aryldibromide with a substituted terminal acetylene compound containing at least three carbon atoms and a hydroxy group on the carbon atom adjacent to the acetylene group in the presence of a dialkyl or trialkyl amine solvent and a catalyst system consisting of a palladium complex containing two halogen moieties and two tri-substituted phosphine moieties. Additional triphenylphosphine can be added. A cuprous iodide promoter is also employed in the reaction sequence. The bromoarylacetylenes can be reacted with a substituted terminal acetylene compound as defined using the same catalyst system as defined to produce the corresponding aryldihydroxy substituted acetylenes. Certain bromophenylhydroxy substituted acetylenes are claimed as new compositions.

REFERENCES:
patent: 2693489 (1954-11-01), Kleinschmidt
patent: 3981932 (1976-09-01), Diamond
patent: 4089908 (1978-05-01), Kathawala
Moroz et al. "Izvest. Akad. Nauk SSSR, Ser. Khim" No. 2, pp. 476-479 (1973).
Moroz et al., "C.A." 78:147456x (1973).
Sonogashira et al., "Tetra Letters", No. 50, pp. 4467-4470 (1975) Pergamon Press.
Curtis et al. "Tetra Letters", No. 25, pp. 2919-2920 (1968) Pergamon Press.

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