Chemical intermediates bearing a trifluoromethyl group

Details Chemical intermediates bearing a trifluoromethyl group Chemical intermediates bearing a trifluoromethyl group

1999-01-26

2000-01-11

Barts, Samuel

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

Organic compounds

Amino nitrogen containing

564271, 564279, 564442, 564462, 564509, 568 35, 568412, 568418, C07C24900, C07C25100, C07C25700, C07C26307

Patent

active

060138386

ABSTRACT:
Novel trifluoromethylated intermediates are provided which are useful in synthesizing trifluoromethylated organic compounds. Specifically, compounds of the formula CF.sub.3 CR are provided, wherein R is (Cl).dbd.CHCH.sub.2 SO.sub.2 Ph, (Cl).dbd.CHCH.sub.2 CH.sub.2 C(.dbd.O)CH.sub.3, (Cl).dbd.CHCH.sub.2 CH(COCH.sub.3).sub.2, (Cl).dbd.CHCH.sub.2 NR'R" or H.dbd.CHCH.dbd.NR'; R' and R" are the same or different and are selected from the group consisting of hydrogen, unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl, unsubstituted or substituted C.sub.3 to C.sub.7 cycloalkyl, unsubstituted or substituted C.sub.2 to C.sub.12 alkenyl, a benzyl group unsubstituted or substituted with R'", or a phenyl group unsubstituted or substituted with R'"; or R' and R" taken together form a five- or six-membered ring; and R'" is an unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl, an unsubstituted or substituted C.sub.1 to C.sub.6 alkoxy, an unsubstituted or substituted C.sub.1 to C.sub.6 thioakyl, a cyano, a halogen, or a C.sub.1 to C.sub.2 dialkylamino group; with the proviso that when the alkyl, cycloalkyl or alkenyl of R' or R" or the alkyl, alkoxy or thioalkyl of R'" is substituted, it may be substituted with any group compatible with amine functionality. The novel compounds are versatile intermediates for the synthesis of a wide variety of trifluoromethylated organic compounds, which have found great utility as pharmaceuticals, agricultural chemicals, and materials such as liquid crystals.

REFERENCES:
patent: 4638091 (1987-01-01), Bowden
patent: 5446217 (1995-08-01), Van Der Puy
patent: 5654473 (1997-08-01), Van Der Puy
Journal of The Chemical Society Perkin Transactions I; "The Peroxide-initiated Addition of 1,1-Dibromotetrafluoroethane to Ethylene, Propene, and 2-Methylpropene" JCPRB4(Sep. 10) 1121-1290(1972).
Principles of Chemistry, "Chemical Properties of the Noble Glass" Raymond E. Davis, 1938.
Journal of Flourine Chemistry, 76 (1996) 49-54 "Preparation, Fluorination and Synthetic Utility of a CFC-Olefin Adduct", Michael Van Der Puy, et al.
Tetrahedron Letters, vol. 32, No. 26, pp. 3071-3074, 1991 "Synthesis of Trifluoromethylalkenes and Alkynes. Trifluoromethyl Captodative Olefins", Andre J. Laurent, et al.
Bull. Chem. Soc. Jpn., 60, 4385-4394 (1987), "Practical, Stereocontrolled Synthesis of Polyfluorinated Artificial Pyrethroids", Makoto Fujita, et al.
J. Org. Chem. 1994, 59, 5692-5699, "New Method for Trifluoromethylation of Enolate Anions and Applications to Regio-,Diastereo-and Enantioselective Trifluoromethylation", Teruo Umemoto, et al.
Tetrahedron Letters, vol. 34, No. 36, pp. 5711-5714, 1993 "Trifluoroethylidenation of Compounds with Activated Methylene Groups", Celal Ates, et al.
Tetrahedron Letters, vol. 33, No. 9, pp. 1221-1224, 1992 Trifluoroacetyltriphenylsilane as a Potentially Useful Fluorine-Containing Building Block. Preparation and its Transformation into 2,2-Difluoro Enol Silyl Ethers, Fuqiang Jin.
Tetrahedron Letters, vol. 33, No. 4 pp. 511-514 1992, Palladium-Catalyzed Cross-Coupling of Trifluoroisopropenylzinc Reagent with Vinyl Halides. A Novel Stereospecific Synthesis of Trifluoromethylated 1,3--Dienes, Biao Jiang, et al.
1989 Bull. Chem. Soc. Jpn., 62, 1352-1354 (1989) vol. 62, No. 4, "A Facile and practical Synthesis of 1-Aryl-3,3,3-trifluoropropynes", Tamejiro Hiyama, et al.
Derwent Publications Ltd., 1-Substd.-2-Chloro-3,3,3-Trifluoropropene-by Reactive e.g. 1-(Chlorophenyl)-Dichlorotri Fluoro Propyl Acetate with Zinc Powder in Aprotic Solvent JP 62228032 A, 871006, 8745.

Affiliated with

Also associated with

Rating

Chemical intermediates bearing a trifluoromethyl group does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Chemical intermediates bearing a trifluoromethyl group, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chemical intermediates bearing a trifluoromethyl group will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1463745