Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-09-13
2005-09-13
Tsang, Cecilia J. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C546S345000, C552S263000, C562S493000, C570S127000, C570S182000, C570S183000, C568S315000, C568S323000, C568S332000, C568S338000, C568S705000, C568S929000, C568S933000, C568S938000
Reexamination Certificate
active
06943257
ABSTRACT:
The present invention provides a process for preparing an aromatic bromide or aromatic iodide from an aromatic amine derivative using nitrite anion and halodimethylsulfonium halide generated in situ from hydrobromic acid/DMSO or hydriodic acid/DMSO. The process for producing compounds of the formula (1) is disclosed (1) wherein X is bromine or iodine: Y is carbon or nitrogen; R1, R2, R3, R4and R5which may be the same or different and are selected independently from the group consisting of a hydrogen, a hologen, a C1-C8alkyl, a C1-C10alkoxy, a nitro, a formyl, an aryl, a benzyl, a C2-C10alkylcarbonyl and an arylcarbonyl, provided that adjacent groups as selected from R1, R2, R3, R4and R5may combine to form a ring.
REFERENCES:
Smith et al., Notes “Application of the Isoamyl Nitrite-Diiodomethane Route to Aryl Iodides”, J. Org. Chem., 1990, vol. 55, No. 8, pp. 2543-2545.
Majetich et al., “Electrophilic Aromatic Bromination Using Bromodimethylsulfonium Bromide Generated in Situ”, J. Org. Chem., 1997, vol. 62, No. 13, pp. 4321-4326.
Braendlin et al., “Halegenation” in “Friedel-Crafts and Related Reactions”, Ed. Olah. G., Interscience Publisher, NY, 1964, vol. III, part 2, p. 1517.
Wulfman, “The Chemistry of Diazonium and Diazo Groups”, Ed. Patai, S., J. Wiley, NY, 1978, part 1, pp. 288-290.
Org. Syn. Coll., vol. 3, 1955, pp. 185-187.
Baik Woon Phil
Kim Jung Min
Kim Shin Jong
Kim Young Sam
Lee Seok Woo
Covington Raymond
Greenblum & Bernstein P.LC.
Tsang Cecilia J.
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