Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1992-07-09
1993-09-28
Reamer, James H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568626, C07C 4545
Patent
active
052488292
ABSTRACT:
This invention is a process for the production of acetylated aromatic products, including acetyl benzoeyclobutenes, in one step and in high yield. The process comprises contacting an aryl halide with an alkyl vinyl ether in the presence of a zerovalent palladium catalyst complex and a hydrogen halide acceptor in a aqueous solvent mixture containing at least about one molar equivalent of water based on moles of the aryl halide.
REFERENCES:
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patent: 3922299 (1975-11-01), Heck
patent: 4070374 (1978-01-01), Chalk et al.
Heck, Organic Reactions, vol. 27, 345-391 (1982).
Hallberg et al., "Palladium-Catalyzed Arylation of Methyl Vinyl Ether," J. Org. Chem., vol. 46, 5414-15 (1981).
Andersson et al., "Synthesis of .beta.-Arylvinyl Ethers by the Palladium-Catalyzed Reaction of Aryl Chlorides with Vinyl Ethers," J. Org. Chem., vol. 53, 235-239 (1988).
Arai et al., "Palladium-Catalyzed Phenylation of Enol Ethers and Acetates," J. Org. Chem., vol. 44, 21-23 (1979).
Andersson et al., "Chelation-Controlled, Palladium-Catalyzed Vinylic Substitution Reactions of Vinyl Ethers. 2-Arylethanal Equivalents from Aryl Halides," J. Org. Chem., vol. 55, 5757-5761 (1990).
Andersson et al., "Regiochemistry of Palladium-Catalyzed Arylation Reactions of Enol Ehers. Electronic Control of Selection for .alpha.- or .beta.-Arylation," J. Org. Chem., vol. 52, 3529-3536 (1987).
Lloyd et al., "The Electrophilic Substitution of Benzocyclobutene-I," Tetrahedron, vol. 20, 2185-2194 (1964).
U.S. patent application Ser. No. 667,023 filed on Mar. 28, 1991 (furnished upon request).
U.S. patent application Ser. No. 676,622 filed on Mar. 28, 1991 (furnished upon request).
O'Keefe Robert M.
Reamer James H.
The Dow Chemical Company
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