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United States Patent (19) 11 Patent Number: 6,080,886 Lal Et Al

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United States Patent (19) 11 Patent Number: 6,080,886 Lal Et Al US00608088.6A United States Patent (19) 11 Patent Number: 6,080,886 Lal et al. (45) Date of Patent: Jun. 27, 2000 54 FLUORINATION WITH AMINOSULFUR Messina, et al., Aminosulfur Trifluorides: Relative Thermal TRIFLUORIDES Stability, Journal of Fluorine Chemistry, 43, (1989), pp. 137-143. 75 Inventors: Gauri Sankar Lal, Whitehall; Guido Peter Pez, Allentown, both of Pa. M. Hudlicky, Fluorination with Diethylaminosulfur Trifluo ride and Related AminofluoroSulfuranes, Organic Reaction, 73 Assignee: Air Products and Chemicals, Inc., vol. 35, (1988), pp. 513–553. Allentown, Pa. G. L. Hann, et al. Synthesis and Enantioselective Fluorode hydroxylation Reactions of 21 Appl. No.: 08/939,940 (S)-2-(Methoxymethyl(pyrrolidin-1-ylsulphur Trifluoride, 22 Filed: Sep. 29, 1997 the First Homochiral Aminofluorosulphurane, J. Chem. Sol., 51 Int. Cl." .......................... C07C 17/013; CO7C 29/62 Chem. Commun. (1989) pp. 1650–1651. 52 U.S. Cl. .......................... 560/227: 544/158; 546/248; J. Cochran, Laboratory, Explosions, Chemical and Engineer 548/562; 548/565; 548/570; 564/102; 568/437; ing News, (1979), vol. 57, No. 12, pp. 4 & 74. 568/821; 570/127; 570/144; 570/125 58 Field of Search ............................ 564/102; 544/158; W. T. Middleton, Explosive Hazards with DAST, Chemical 546/248; 548/562, 565, 570; 570/142, 127, and Engineering News, (1979), vol. 57, No. 21, p. 43. 144, 175; 560/227; 568/437, 821 W. J. Middleton, et al., a,a-Difluoroarylacetic Acids: Prepa ration from (Diethylamino)sulfur Trifluoride and X-Oxary 56) References Cited lacetates, J. Org. Chem. (1980) 45, 2883-2887. U.S. PATENT DOCUMENTS 3,499,030 3/1970 Kuhle et al. ............................ 260/551 Primary Examiner-Peter O'Sullivan 3,914.265 10/1975 Middleton ... ... 260/397 3,976,691 8/1976 Middleton ............................... 260/544 Attorney, Agent, or Firm-Geoffrey L. Chase FOREIGN PATENT DOCUMENTS 57 ABSTRACT 433136 12/1974 Russian Federation. A fluorination method of oxygen and halogen Sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl OTHER PUBLICATIONS and cyclic aminoSulfur trifluorides fluorinating reagents is W. J. Middleton, New Fluorinating Reagents, Dialkylami disclosed. nosulfur Fluorides, J. Org. Chem., vol. 40, No. 5, (1975), pp. 574-578. 20 Claims, No Drawings 6,080,886 1 2 FLUORINATION WITH AMINOSULFUR carbonyl to gem-difluoride transformation is usually carried TRIFLUORIDES out at room temperature or higher. Numerous Structurally diverse aldehydes and ketones have been Successfully flu CROSS-REFERENCE TO RELATED orinated with DAST. These include acyclic, cyclic, and APPLICATIONS aromatic compounds. Elimination does occur to a certain Not applicable. extent when aldehydes and ketones are fluorinated and olefinic by-products are also observed in these instances. STATEMENT REGARDING FEDERALLY While the DAST compounds have shown versatility in SPONSORED RESEARCH OR DEVELOPMENT effecting deoxofluorinations, there are Several well recog nized limitations associated with their use. The compounds Not applicable. can decompose violently and while adequate for laboratory Synthesis, they are not practical for large Scale industrial use. BACKGROUND OF THE INVENTION In Some instances, undesirable by-products are formed dur The development of Safe, efficient, and Simple methods 15 ing the fluorination proceSS. Olefin elimination by-products for Selective incorporation of fluorine into organic com have been observed in the fluorination of Some alcohols. pounds has become a very important area of technology. Often, acid-catalyzed decomposition products are obtained. This is due to the fact that fluorine Strategically positioned The reagent's two step method used for their Synthesis at Sites of Synthetic drugs and agrochemical products Sig renders these relatively costly compositions only Suitable for nificantly modifies and enhances their biological activities. Small Scale Syntheses. The conversion of the C-O to the C-F bond, which is The DAST reagents are recognized as fluorinating referred to herein a deoxofluorination, represents a viable reagents in U.S. Pat. Nos. 3,914,265 and 3,976,691. method to produce Selectively fluorinated organic Additionally, Et-DAST and related compounds have been discussed in W. J. Middleton, New Fluorinating Reagents. compounds, but the low yields and hazards associated with 25 the current deoxofluorination reagents and processes Dialkylaminosulfur Fluorides, J. Org. Chem., Vol. 40, No. 5, Severely limit the application of this technique. (1975), pp 574-578. However, as reported by Messina, et al., Aminosulfur Trifluorides: Relative Thermal Stability, The introduction of fluorine into medicinal and agro Journal of Fluorine Chemistry, 43, (1989), pp 137-143, chemical products can profoundly alter their biological these compounds can be problematic fluorinating reagents properties. Fluorine mimics hydrogen with respect to Steric due to their tendency to undergo catastrophic decomposition requirements and contributes to an alteration of the elec tronic properties of the molecule. Increased lipophilicity and (explosion or detonation) on heating. See also reports on this oxidative and thermal stabilities have been observed in Such by J. Cochran, Laboratory Explosions, Chemical and Engi fluorine-containing compounds. neering News, (1979), vol. 57, No. 12, pp. 4 & 74; and W. 35 T. Middleton, Explosive Hazards with DAST, Chemical and In View of the importance of organofluorine compounds, Engineering News, (1979), vol. 57, No. 21, p. 43. Difficul efforts aimed at the development of Simple, Safe, and effi ties with major amounts of by-products in the fluorination cient methods for their Synthesis have escalated in recent reaction is also noted. See also M. Hudlicky, Fluorination years. The conversion of the carbon-oxygen to the carbon 40 with Diethylaminosulfur Trifluoride and Related fluorine bond by nucleophilic fluorinating Sources Aminofluorosulfuranes, Organic Reaction, Vol. 35, (1988), (deoxofluorination) represents one Such technique which has pp. 513–553. been widely used for the selective introduction of fluorine Further, Russian Inventor's Certificate No. 433,136 pub into organic compounds. A list of the deoxofluorination lished Dec. 15, 1974 discloses sulfur dialkyl(alkylaryl) methods practiced to date includes: nucleophilic Substitution 45 aminotrifluorides. via the fluoride anion; phenylsulfur trifluoride; fluoroalky lamines; Sulfur tetrafluoride; SeF; WF; difluorophospho G. L. Hann, et. al., in Synthesis and Enantioselective ranes and the dialkylaminosulfur trifluorides (DAST). The Fluoro dehydroxylation Reactions of (S)-2- most common reagent of this class is diethylaminoSulfur (Methoxymethyl)pyrrolidin-1-ylsulphur Trifluoride, the 50 First Homochiral Aminofluorosulphurane, J.Chem. Soc., trifluoride, Et-DAST or simply DAST. Chem. Commun. (1989) pp 1650–1651, disclosed the ami The DAST compounds have proven to be useful reagents nosulfur trifluorides, (S)-2-(methoxymethyl)pyrrolidin-1- for effecting deoxofluorinations. These reagents are conven ylsulphur trifluoride and N-morpholinosulphur trifluoride as tionally prepared by reaction of N-silyl derivatives of 2 fluorinating reagents for 2-(trimethylsiloxy)Octane. amines with SF. In contrast to SF, they are liquids which 55 The method and compositions of the present invention can be used at atmospheric pressure and at near ambient to overcome the drawbacks of the prior art fluorinating relatively low temperature (room temperature or below) for reagents, including DAST, by providing more thermally most applications. Deoxofluorination of alcohols and stable fluorine bearing compounds which have effective ketones are particularly facile and reactions can be carried 60 fluorinating capability with far less potential of Violent out in a variety of organic Solvents (e.g., CHCl, CFCl, decomposition and attendant high gaseous by-product glyme, diglyme, CH2Cl2, hydrocarbons, etc.). Most fluori evolvement, with Simpler and more efficient fluorinations, as nations of alcohols are done at -78 C. to room temperature. will be set forth in greater detail below. Various functional groups are tolerated including CN, BRIEF SUMMARY OF THE INVENTION CONR, COOR (where R is an alkyl group), and successful 65 fluorinations have been accomplished with primary, Second The present invention is a method for the fluorination of ary and tertiary (1,2,3) allylic and benzylic alcohols. The a compound using a fluorinating reagent comprising con 6,080,886 3 4 tacting the compound with the fluorinating reagent under Preferably, the composition used as the fluorinating conditions Sufficient to fluorinate the compound wherein the reagent has the Structure: fluorinating reagent is an aminoSulfur trifluoride composi tion having a structure with one or more: wherein R' are individually H, normal or branched SF alkyl Co or aryl Co and R" are Cao normal or branched alkyl. N Alternatively, the composition used as the fluorinating 1-(- SR)- reagent has the Structure: wherein m=1-5 and R' and R are: RORN(SF)ROR (1) when m=1, individually aryl or meta- or para wherein R and Rare individually C, to Co. in a normal or Substituted aryl radicals in which the meta- or para branched chain alkyl and R' and R are C-do normal or Substitution is Selected from the group consisting of 15 branched alkyl. normal and branched Co, trifluoromethyl, alkoxy, More preferably, the composition used as the fluorinating aryl Co., nitro, Sulfonic ester, N,N-dialkylamino and halogens, or reagent
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