Synthesis of bromobiphenyls

Details Synthesis of bromobiphenyls Synthesis of bromobiphenyls

1992-07-17

1993-10-19

Lone, Werren B.

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

Organic compounds

Halogen containing

570182, 570183, 570192, C07C 2518

Patent

active

052547760

ABSTRACT:
Bromobiphenyls (such as 2-fluoro-4-bromobiphenyl) are synthesized by reacting together a phenylboronic acid (such as phenylboronic acid) and a bromoiodobenzene (such as 2-fluoro-4-bromoiodobenzene). The reaction generally takes place with the aid of a catalyst (such as palladium in a zero valance state) and an inert solvent (such as fluorobenzene). Control of temperature is very important to obtain both an acceptable reaction rate and an acceptable level of terphenyl byproduct.

REFERENCES:
patent: 3006972 (1961-10-01), Fields et al.
patent: 3341569 (1967-09-01), Sharnes
patent: 3401207 (1968-09-01), Selwitz
patent: 3978144 (1976-08-01), Eilingsfeld et al.
N. Miyaura et al., The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases, Synthetic Communications, 11(7) pp. 513-519 (1981).
R. Miller, et al., Stoichiometric Synthesis of Unsymmetrical Mononitrobiphenyls via the Palladium-Catalyzed Cross-Coupling . . . with Aryl Bromides, Organometallics, (3), pp. 1261-1263, (1984).
W. Thompson, et al., A General Synthesis of 5-Arylnicotinates, J. Org. Chem., (49) pp. 5237-5243 (1984).
M. Sharp, et al., Synthetic Connections to the Aromatic Directed Metalation Reaction, Tetrahedron Letters, vol. 28, No. 43, pp. 5093-5096 (1987).
Washburn, et al., Preparation, Properties, and Uses of Benzene Boronic Acid, Metal-Organic Compounds (ACS Advances in Chemistry Series No. 23), pp. 102-128 (1959).

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