Process for producing trifluoromethyl- substituted 2-...

Details Process for producing trifluoromethyl- substituted 2-... Process for producing trifluoromethyl- substituted 2-...

2006-05-30

2006-05-30

Solola, Taofiq (Department: 1626)

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

Organic compounds

Oxygen containing

Reexamination Certificate

active

07053248

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
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-Acetol-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-Sybstituted α-Methoxyacetophenones”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.
Ashby et al., “The reaction of benzotrihalides and benzal halides with magnesium. Synthetic and mechanistic studies”,J. Organometallic Chem., (1990) 390:275-292.
Ferraboschi et al., “Baker's Yeast-Mediated Reduction of α-Hydroxy Ketones andDerivatives: The Steric Course of the Biotransformation”. Tetrahedron (1994) vol. 50, No. 35, pp. 10539-10548.
Posner et al., “Methyl and n-alkyl ketones from carboxylic acid chlorides and organocopper 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.

Affiliated with

Also associated with

Rating

Process for producing trifluoromethyl- substituted 2-... 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 2-..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing trifluoromethyl- substituted 2-... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3631486