1- Methyl-3-phenyl-5- 3-trifluoromethyl

Fluridone, 1-methyl-3-phenyl-5-(3-trifluoromethyl-phenyl)-4(1H)-pyridinone (Eli Lilly). 

Sonar. See 1-Methyl-3-phenyl-5-[3-(trifluoromethyl) phenyl]-4( 1 H)-pyridinone Sonojell No. 4 Sonojeli No. 9. See Petrolatum... 

Isopropanolamine 2-Mercaptoethanol 1-Methyl-3-phenyl-5-[3-(trifluoromethyl) phenyi]-4(1 H)-pyridinone a-Naphthylamine Nitrosophenylhydroxylamine ammonium salt Phenyl benzoate m-Phenylenedimaleimide N-Phenylmaleimide Phenyl mercuric bromide Potassium carbonate Potassium N-hydroxymethyl-N-methyldithiocarbamate Pyridine Silica, fused Tetrachlorophthalic acid Thiourea p-Toluic acid , N-Tridecyl-2,6-dimethylmorpholine Trimethyl phosphate agric. chemicals, maleic hydrazide Hydrazine agric. sprays Zinc sulfate monohydrate agric., biodegradable Poly (hydroxybutyrate-hydroxyvalerate) agriculture... 

The enantiomeric excess (ee) of the hydrogenated products was determined either by polarimetry, GLC equipped with a chiral column or H-NMR with a chiral shift reagent. Methyl lactate and methyl 3-hydroxybutanoate, obtained from 1 and 2, respectively, were analized polarimetry using a Perkin-Elmer 243B instrument. The reference values of [a]o(neat) were +8.4° for (R)-methyl pyruvate and -22.95° for methyl 3-hydroxybutcinoate. Before GLC analysis, i-butyl 5-hydroxyhexanoate, methyl 5-hydroxyhexanoate, and n-butyl 5-hydroxyhexanoate, obtained from 1, 5, and 6, respectively, were converted to the pentanoyl esters, methyl 3-hydroxybutanoate was converted to the acetyl ester, and methyl 4-methyl-3-hydroxybutanoate obtained from 2 was converted the ester of (+)-a-methyl-a-(trifluoromethyl)phenyl acetic acid (MTPA). 

Silver(I) complexes are known with the tris(pyrazolyl)borate [HB(pz)3] and the methyl, phenyl, bromo, or trifluoromethyl-substituted derivatives. The structure of the silver tri(pyrazolyl)borato species has been a puzzle since it was first reported.385,386 It was suggested that the structure could be oligomeric, but recently the crystal structure of the compound [Ag HB(3,5-Me2pz)3 ]2 shows that it has a dimeric structure387 where the silver(I) centers are tricoordinated by a bidentate arm of one ligand and a monodentate arm of the other ligand (29). The related complexes [Ag HB(4-Brpz)3 ]2, [Ag HB(4-Mepz)3 ]2, [Ag HB(3,5-Me2pz)3 ]2, [Ag HB(3-Mepz)3 ] , [Ag B(pz)4 ], and... 

Two convenient methods have been developed for the preparation of trifluoro-methyl-substituted alkoxyallenes. Reductive elimination of allylic acetates 30 with samarium diiodide leads to 31 (Scheme 8.11) [38], whereas reaction of Wittig cumu-lene 32 with phenyl trifluoromethyl ketone (33) and thermolysis of the intermediate 34 provides 35 (Scheme 8.12) [39]. 

The dipolarophile was prepared in a short (three-step) sequence from methyl phenyl sulfone (38% overall yield) and ethyl trifluoroacetate. Desulfonation, followed by reductive N-0 cleavage afforded the syn aminoalcohols [246]. Conjugate additions to the sulfone were described some years earlier [247] more recently, trifluoromethyl pyrroles have been synthesised from the nitro-propene [248]. 

Chlorine atoms in (trichloromethyl)benzenes which have fluoro, chloro, dichloromethyl, chloroformyl, cyano, isocyanato, jV-phthalimino or methyl substituents in the ring are substituted by fluorine using antimony(III) fluoride (Swarts reaction).3 4 2-(Trifluoromethyl)phen-yl isocyanate, 4-chloro-2-(trifluoromethyl)phenyl isocyanate, 2,4- and 2,5-bis(trifluoro-methyl)phenyl isocyanate, and 2,4-bis(trifluoromethyl)-l,5-phenylenc diisocyanate can be obtained in this way.5... 

Chlorine atoms are easily substituted by fluorine in methyl- and polymethyl(trichloro-methyl)benzenes with evolution of heat to give l-methyl-2-(trifluoromcthyl)benzene,8 4-chloro-2-methyl-l-(trifluoromethyl)benzene,9 4-chloro-l-methyl-2-(trifluoromethyl)benzenc.10 1,3,5-trimethyl-2-(trifluoromethyl)benzene,11 I. S -tctramethyl-S trifluoromethyObenzene,11 and 2-methyl-4-phenyl-l-(trifluoromethyl)benzene8 in 50-60% yield. 

Phenylmercury(II) fluoride-hydrogen fluoride complex fluorinates phenyl(tribromo-methyl)mereury in 60-65% yield when the reaction is carried out in the presence of 48% hydrogen fluoride. Phenyl(trichloromethyl)mercury can be fluorinated to the trifluoromethyl derivative in this manner, but a reaction temperature of 90 C is required. Partial fluorination of (bromodichloromethyl)phcnylmcrcury to (dichlorofluoromethyl)phenylmercury in 60% yield can be achieved at room temperature, but attempted partial fluorination of phenyl(tri-bromomethyl)mercury, (dibromochloromethyl)phenylmercury, and (dibromofluoromethyl)-phenylmereury was unsuccessful phenyl(trifluoromethyl)mercury is the major product obtained.61... 

Bis-[trifluoromethyl]-4-(4-methyl-phenyl)-6-triehloromethyl- E14a/ 2, 754 (R2CO + R-CS NH2/ Cl3C-CHO)... 

X4 is -0S02R6 where R6 is methyl, trifluoromethyl, phenyl, p-methyl phenyl, 2-, 4-, 6-trimethylphenyl, 2- naphthyl, or 2-pyridyl with 1-15 moles of a non-gaseous inorganic fluoride in a polyglycol having at least four alkylidene oxide units at a temperature of 40°C to 150°C and retaining said compound of formula III formed in the reaction mixture until completion of the reaction. 

CiiHisBiCliF O 1 -Chloro-1 -(4-methylphenyl)-3,3-bis(trifluoromethyl)-1 -[4-(trifluoro-methyl)phenyl]-3//-2,1 -benzoxabismole 6.6-39 S ... 

CARBENES, GENERATION Chloral. Dibromofluoromethane. Dimethoxy-methyl)trimethoxysilane. Dimethyl diazomethylphosphonate. S -Dimethyl-N-nitroso-2-oxazolidone. Ethylidene iodide-Diethylzinc. Ethyl trichloroacetate. Phenyl(dibromochloro methyl) mercury. Phenyl(dihalocarbomethoxymethyl)mer-cury. Phenyl(trifluoromethyl)mercury. Phenyl(trihalomethyl)mercury. Sodium chlorodiiluoroacetate. Zinc powder. 

Organic fluorine compounds and methods for their preparation are the central topic of the next four procedures. Much of the synthetic versatility of methyl phenyl sulfone is embodied in FLUOROMETHYL PHENYL SULFONE and the fluoro Pummerer reaction of methyl phenyl sulfoxide with DAST is a key step in its preparation. The utility of this fluoromethyl sulfone in the preparation of fluoroalkenes Is demonstrated in a companion procedure for Z-[2-(FLUOROMETHYLENE) CYCLOHEXYL]BENZENE, a procedure with several prominent stereoselective features. Geminal difluoroalkenes are featured in the following procedure. (3,3 DIFLUOROALLYL)TRIMETHYLSILANE is prepared by a method in which the radical addition of dibromodifluoromethane to alkenes and the selective reduction of a-bromoalkylsilanes are key steps. A procedure for nucleophilic introduction of the trifluoromethyl group completes this set. The key reagent, (TRIFLUOROMETHYL)-TRIMETHYLSILANE is obtained by reductive coupling of TMS chloride and bromotrifluoromethane. Liberation of a CF3- equivalent with fluoride ion in the presence of cyclohexanone affords 1-TRIFLUOROMETHYL-1-CYCLOHEXANOL. 

Benfluorex, 2-[ ]-Methyl-2-[3-(trifluoromelhyl)-phenyl]ethyl]amino ethanol benzoate (ester) 2-[[a-methyl-m-(trifluOromethyl)phenethyl amino]alhanol benzoate (ester) ... 

Phenyl isothiocyanate 4-Nitrophenyl isothiocyanate Trifluoromethyl phenyl isothiocyanate 4-Cyanophenyl isothiocyanate 4-Methoxyphenyl isothiocyanate 4-Fluorophenyl isothiocyanate 4-Methylphenyl isothiocyanate 2-Fluoro-5-(trifluoromethyl)phenyl isothiocyanate 4-Methyl-3-(trifluoromethyl)phenyl isothiocyanate 4-Fluoro-3-(trifluoromethyl)phenyl isothiocyanate 3,5-Bis(trifluoromethyl)phenyl isothiocyanate 1,4-Phenylene diisothiocyanate... 

Methyl-3-(trifluoromethyl)phenyl isothiocyanate Figure 2.25 Isothiocyanates. 

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