Production of brominated methoxynaphthalene compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C07C 4122

Patent

active

058409963

ABSTRACT:
Bromine is generated in situ in a mixture formed by mixing together 2-methoxynaphthalene, hydrogen bromide, at least one peroxidic compound and a chemically indifferent organic liquid solvent or diluent under conditions effective to produce 1,6-dibromo-2-methoxynaphthalene. Optionally, but preferably, water is also included in the mixture. Regioselective hydrodebromination of 1,6-dibromo-2-methoxynaphthalene with hydrogen and tungsten carbide enables production of 2-bromo-6-methoxynaphthalene.

REFERENCES:
patent: 4628123 (1986-12-01), Borsotti
patent: 5243088 (1993-09-01), Jacquot et al.
patent: 5256829 (1993-10-01), Jacquot
patent: 5412150 (1995-05-01), Wessel
patent: 5426243 (1995-06-01), Lecouve
Bray, et al., "The Catalytic Decomposition of Hydrogen Peroxide in a Bromine-Bromide Solution, and a Study of the Steady State", J. of Am. Chem. Soc., 1923, v. 45, pp. 1251-1280.
Choudary, et al., "Regioselective Oxybromination of Activated Aromatic Compounds Catalyzed by Ammonium Molybdate", Synlett, 1994, pp. 450.
Kajigaeshi, et al., "Halogenation Using Quaternary Ammonium Polyhalides, IV, Selective Bromination of Phenols by Use of Tetraalkylammonium Tribromides", Bull. Chem. Soc. Jpn. 1987, v. 60, pp. 4187-4189.
Kornblum, et al., "Solvation as a Factor in the Alkylation of Ambident Anions: The Importance of the Hydrogen Bonding Capacity of the Solvent", J. Am. Chem. Soc., 1963, v. 85, pp. 1141-1147.
March, Advanced Organic Chemistry, Reactions, Mechanisms, and Structure, 3rd Ed., Wiley-Interscience Publication, pp. 322-325, 1985.
Marques, et al., "Facile Hydrodehalogenation with H.sub.2 and Pd/C Catalyst under Multiphase Conditions. . . .", J. Org. Chem., 1995, v. 60, pp. 2430-2435.
Pinder, "The Hydrogenolysis of Organic Halides", Synthesis, 1980, pp. 425-452.
Rajagopal, et al., "Mechanism of Palladium-Catalyzed Transfer Hydrogenolysis of Aryl Chlorides by Formate Salts", J. Org. Chem., 1995, vol. 60, pp. 1347-1355.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Production of brominated methoxynaphthalene compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Production of brominated methoxynaphthalene compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Production of brominated methoxynaphthalene compounds will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1704648

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.