Process for producing trifluoromethyl-substituted...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

11347390

ABSTRACT:
A process for producing a brominated acetal (represented by the formula 3) includes (a) brominating a trifluoromethyl-substituted acetophenone by Br2in the presence of an alkylene diol. It is optional to produce a trifluoromethyl-substituted 2-alkoxyacetophenone derivative (represented by the formula 9) by (b) reacting the brominated acetal with a metal alkoxide, thereby converting the brominated acetal into an ether; and (c) hydrolyzing the ether in the presence of an acid catalyst to remove an acetal group from the ether, thereby producing the 2-alkoxyacetophenone derivative. Alternatively, the 2-alkoxyacetophenone can be produced by (a) reacting a trifluoromethyl-substituted phenacyl halide with an acetalization agent, thereby converting the phenacyl halide into an acetal; (b) reacting the acetal with a metal alkoxide, thereby converting the acetal into an ether; and (c) hydrolyzing the ether in the presence of an acid catalyst to remove the acetal group from the ether

REFERENCES:
patent: 3717655 (1973-02-01), Godefrol et al.
patent: 0 080 071 (1983-06-01), None
patent: 1 209 150 (2002-05-01), None
patent: 2001-072638 (2001-03-01), None
patent: WO 01/17962 (2000-08-01), None
Sekimata et al, J. Agric. Food Chem., (2002) vol. 50(12), pp. 3486-3490 (published on the Web May 4, 2002).
G. Solladie et al, Asymmetric Synthesis of Polyhydroxylated Natural Products I. Efficient Preparation of L-Arabinitol, vol. 28, No. 1, 1987, pp. 61-64, XP0001079307, p. 62, scheme 2.
S. Rozen et al., “A Novel Electrophilic Methoxylation (With a Little Help From F2)”, J. Am.Chem. Soc., vol. 114, No. 20, 1992, pp. 7643-7645, XP002260560, scheme II, conversion 15-8.
Database Crossfire, XP-002260564, J. Toullec et al., “Kinetics and Mechanism of the Acid-Catalyzed Bromination of Ring-Substituted Acetophenones in Methanol. Thermodynamics of the Ketone-Acetal-Enol Ether System in Methanol and Water1”, J. Org. Chem, vol. 51, No. 21, 1986, pp. 4054-4061, XP002260561.
M. Andersen et al., Electrochemistry of Electron Transfer Probes. Observation of the Transition from Activation to Counterdiffusion Control in the Fragementation of α-Aryloxyacetophenone Radical Anions1a, J. Am. Chem. Soc., vol. 119, No. 28, 1997, pp. 6590-6595, XP002260563, p. 6593, Column 1, p. 6595, Column 2. compounds IVd-e.
Camuzat-Dedenis et al., “Reaction of Phosphonium Ylides and Aromatic Nitriles under Lewis Acid conditions: an Easy Access to Aryl-substituted α-Methoxyacetophenonews” Synthesis (1999) No. 9 pp. 1558-1560.
Lewis et al., “Molecular Photochemistry. XVIII. Type II Photoelimination and 3-Oxetanol Formation from α-Alkoxyacetophenones and Related Compounds” J. Am. Chem. Soc. (1970) 92:311-320.
Ferraboschi et al., “Baker's Yeast-Mediated Reduction of α-Hydroxy Ketones and Derivatives: The Steric Course of the Biotransformation” Tetrahedron (1994) vol. 50, No. 35, pp. 10539-10548.
Ashby et al., “The reaction of benzotrihalides and benzal halides with magnesium. Synthetic and mechanistic studies”. J. Organometallic Chem., (1990) 390:275-292.
Posner et al., “Methyl and n-alkyl ketones from carboxylic acid chlorides an organocoper reagents” Tetrahedron Letters, No. 53, pp. 4647-4650, (1970).
Greene et al., “Protection for the Carbonyl Group”, Protective Groups in Organic Synthesis, Third Edition (1999) pp. 293-368.
Chinese Office Action with English Translation dated Jul. 7, 2006. (Ten (10) Pages).

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

Process for producing trifluoromethyl-substituted... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for producing trifluoromethyl-substituted..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing trifluoromethyl-substituted... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3745990

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