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CAS No. : | 2923-16-2 | MDL No. : | MFCD00013215 |
Formula : | C2F3KO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CUNPJFGIODEJLQ-UHFFFAOYSA-M |
M.W : | 152.11 | Pubchem ID : | 23662811 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 11.75 |
TPSA : | 40.13 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.58 cm/s |
Log Po/w (iLOGP) : | -3.36 |
Log Po/w (XLOGP3) : | 0.91 |
Log Po/w (WLOGP) : | 0.56 |
Log Po/w (MLOGP) : | 0.27 |
Log Po/w (SILICOS-IT) : | 0.93 |
Consensus Log Po/w : | -0.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.29 |
Solubility : | 7.79 mg/ml ; 0.0512 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.34 |
Solubility : | 6.98 mg/ml ; 0.0459 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.08 |
Solubility : | 126.0 mg/ml ; 0.826 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In acetonitrile at 20℃; for 48 h; Stage #2: With sulfuric acid In water Stage #3: at 20℃; for 1 h; |
Example 14: Potassium salt of trifluoroacetic acid (CF3-COOK (5)); 20 ml water, 73 ml MeCN, 1.33 g KBr, TEMPO (0.46 g), and 10 g of trifluoroethanol are placed in a 500 ml glass flask equipped with a dropping funnel and stirrer. 175ml of 15percent> wt. aq. NaOCl buffered to pH 8-9 were added via the dropping funnel in 3 portions over two days while stirring at room temperature. Concentrated sulphuric acid and water were added to make the reaction mixture acidic (pH 1 to 2). The reaction mixture was extracted three times with diethyl ether. The combined ether phases were dried over magnesium sulphate and then distilled at atmospheric pressure. Methanol (60 ml) and potassium methoxide (7 g) were added to the distillate and the mixture was stirred for one hour at room temperature, filtered and evaporated to give a colorless solid (13.13 g) Yield: 86percent. 19F NMR (D20): -76.82 (s, 3F). |
86% | With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In water; acetonitrile at 20℃; aq. buffer | General rocedure: 5.5 ml of aq. solutions of KBr (0.55 mol/dm3), 20 ml MeCN, TEMPO (0.12 g, 0.00077 mol), and 2,2,3-trifluoro-3-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-propan-1-ol (2a) (10 g, 0.0275 mol) were placed in the flask. 14percent aq. NaOCl (48 ml) buffered by NaHCO3 (5.2 g) were added via the dropping funnel in 3 portions during two days of stirring in a room temperature (slight exothermic effect). The progress of reaction was monitored by 19F NMR spectroscopy. Then concentrated sulfuric acid followed by water was added. After extraction with diethyl ether, the organic phases were dried over magnesium sulfate. The solvent was evaporated to give a colorless liquid, which was distilled. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | at 20℃; for 12 h; | K(B3N3Me6)CF3 (2 mmol, 0.2 M stock in DMSO) was placed in a Fisher-Porter tube with a small stirbar. The vessel was charged with 60 psi carbon dioxide, and stirred. A pressure drop to 6 psi was observed along with the precipitation of copious white solid. The reaction was stirred at room temperature for 12 hours. After this time, the reaction mixture was extracted with pentane ( x 10 mL). The combined pentane extracts were dried over anhydrous calcium chloride to remove trace DMSO, then filtered and evaporated under high vacuum to afford hexamethylborazine in 95percent yield(314 mg, 1.91 mmol). 1H-NMR (CDC13): 2.86 (a, 9H, s), 0.47 (13, 9H, s). 13C-NMR: 34.52, 0.03 (broad). 11B.NMR: 36.52 (s). HRMS (ES+): 165.1781 (M+: 165.1780). Recovered Hexamethylborazine:The DMSO phase was evaporated overnight at 25 °C in a sublimation apparatus with a coldfinger cooled to 2 °C under dynamic vacuum (0.1 mTorr). The residual solid was then extracted into water, and this was then carefully dried in a scintillation vial to give potassium trifluoroacetate as an off-white solid in 93percent yield (285 mg, 1.86 mmol). 13C{19F}NMR (D20): 162.90, 116.32. 19FNMR (D20): -75.40 (s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With copper(l) iodide; In DMF (N,N-dimethyl-formamide); at 115℃; for 50h;Heating / reflux; | The title compound was prepared in a manner analogous to that described in Example 2. The requisite 1-[2-methoxy-3-(trifluoromethyl)-5,6,7,(at)-tetrahydronaphthalen-1-yl]-N methylmethanamine_was synthesized in a manner analogous to that described for 3-methoxy- 4- [(methylamino)methyl]-2-naphthonitrile. MS m/z 274.2 (M+H)+. The requisite 1-(bromomethyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydronaphthalen-2-yl methyl ether was synthesized using the following method. [2-Methoxy-3-(trifluoromethyl)-5,6,7,8-tetrahydronaphthalen-1-yl]methanol (421 mg, 1.61 mmol) was dissolved in THF (20 mL) and placed an in ice water bath. CBr4 (644 mg, 1.93 mmol) was added followed by addition of PPh3 (509 mg, 1.93 mmol) in portions. Reaction was allowed to warm to room temperature over night. The solids were filtered off through a pad of diatomaceous earth and the filtrate was diluted with EtOAc (25 mL), washed with H20 (10 mL) and brine (5 mL). The organic phase was dried over Na2S04, filtered through a pad of diatomaceous earth and the volatiles removed under reduce pressure. Chromatography of the residue on Si02 (0-20percent EA: HEX)) afforded the title compound (300 mg, 60 percent). 1H NMR (300.132 MHz, CDC13) No. 7.28 (s, 1H), 4.60 (s, 2H), 3.98 (s, 3H), 2.86 (t, J= 6.1 Hz, 2H), 2.77 (t, J= 6.1 Hz, 2H), 1.92 - 1.75 (m, 4H). The requisite [2-methoxy-3-(trifluoromethyl)-5,6,7,8-tetrahydronaphthalen-1-yl]methanol was synthesized using the following method. 2-Methoxy-3 trifluoromethyl-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid methyl ester (519 mg, 1.80 mmol) was dissolved in ether (25 mL) and cooled in an ice water bath. LAH (136 mg, 3.6 mmol) was slowly added under nitrogen in portions and reaction stirred at 0 °C for 2 h. Reaction was quenched with Na2S04 (sat, aq, 4 mL) and stirred for 20 min. Solid Na2S04 (300 mg) was added and mixture filtered through a pad of diatomaceous earth. The filtrate was diluted with EtOAc (25 mL), washed with H20 (10 mL) and brine (5 mL). The organic phase was dried over Na2S04, filtered through a pad of diatomaceous earth and the volatiles removed under reduce pressure. Chromatography of the residue on Si02 (0-50percent EA: HEX)) afforded the title compound (421 mg, 90 percent). MS m/z 243.1 (M+H-OH)+. 1H NMR (300.132 MHz, DMSO) 8 7.28 (s, 1H), 4.95 (s, 1H), 4.53 (s, 2H), 3.80 (s, 3H), 2.92 - 2.88 (m, 2H), 2.76 - 2.72 (m, 2H), 1.75 - 1.70 (m, 4H). The requisite methyl 2-methoxy-3-(trifluoromethyl)-5,6,7,8-tetrahydronaphthalene-1- carboxylate was prepared by the following method. A suspension containing 3-bromo-2-methoxy-5,6,7,8-tetrahydro-naphthalene-l- carboxylic acid methyl ester (2.0g, 6.69 mmol), <strong>[2923-16-2]potassium trifluoroacetate</strong> (1.96g, 10 mmol), copper (1) iodide (2.67g, 14 mmol), and dry DMF (50 mL) was heated to reflux for 2 h. Temperature was reduced to 115 °C. and held for 48 h. The reaction was cooled to room temp and poured into dilute aqueous HCl (2N, 150 mL). This slurry was vacuum filtered through a medium sintered glass filter using ethyl acetate washes (6x30mL). The combined filtrates were washed with IN aq. HCl (100 mL), saturated sodium thiosulfate (100mL), and then sat. aq. brine (100 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified by flash silica gel chromatography (3:1 hexane/methylene chloride then'3:2 hexane /methylene chloride) to give the title compound (0.67g, 35percent yield) as a tan oil. MS m/z 289 (M+H). 1H NMR (300.132 MHz , CDC13) 8 7.30 (s, 1H), 3.92 (s, 3H), 3.84 (s, 3H), 2.70 (m, 4H), 1.78 (m, 4H). 19F NMR (CDCl3) No.-60.44 (s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; toluene; | c Methyl 2-chloro-4-fluoro-5-trifluoromethylbenzoate 12.5 g of methyl 2-chloro-4-fluoro-5-iodobenzoate, 11.2 g of <strong>[2923-16-2]potassium trifluoroacetate</strong> and 15.6 g of Cul were suspended in 320 ml of DMF and 240 ml of toluene and the toluene was distilled off to remove traces of water. The reaction mixture was refluxed for 2 hours, then poured onto 1 l of a half-concentrated aqueous NaHCO3 solution and extracted 4 times using 350 ml of EA each time. The organic phase was dried over Na2 SO4 and the solvent was removed in vacuo. Chromatography on silica gel using EA/HEP 1:8 yielded 860 mg of a viscous oil. Contains an inseparable amount of methyl 2-chloro-4-fluoro-5-iodobenzoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; water; N,N-dimethyl-formamide; | 3. A solution of 23.1 g of 3beta-stigmastanyl 3-bromopropionate in 400 ml of methylene chloride and 200 ml of DMF is treated with 63.3 g of <strong>[2923-16-2]potassium trifluoroacetate</strong> and heated at 80° C. over 72 hours. After adding 30 ml of water the solution is heated at 80° C. for a further 1 hour. The solution is evaporated and the residue is chromatographed on silica gel using ether-hexane. There is obtained 3beta-stigmastanyl 3-hydroxypropionate of melting point 152°-153° C., the starting material of Example 20. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(I) iodide; In N-methyl-acetamide; diethyl ether; water; toluene; | A. Preparation of Formula (9) where Z is trifluoromethyl, R1 and R2 are methyl, and R5 and R6 are hydrogen A suspension containing 6-bromo-2,2,3-trimethyl-2H-1-benzopyran (38.0 g, 0.15 mol), <strong>[2923-16-2]potassium trifluoroacetate</strong> (62.0 g, 0.408 mol) and cuprous iodide (57.0 g, 0.30 mol) in dimethylformamide (530 ml) and toluene (225 ml) was heated under nitrogen until a total of 70 ml of toluene was collected by distillation. Toluene was distilled off until the temperature of the reaction mixture reached 149° C. After a further four hours at this temperature the mixture was cooled to room temperature, water and diethyl ether were added, and the organic phase separated and evaporated under reduced pressure. The residue was chromatographed on silica gel, eluding with heptane to give 18.82 g of 6-trifluoromethyl-2,2,3-trimethyl-2H-1-benzopyran as an oil, ms 242 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 8 Preparation of trifluoroacetyl iodide and potassium trifluoroacetate by reaction of potassium iodide with trifluoroacetic anhydride. With exclusion of moisture, 37.48 g (0.226 mole) of potassium iodide and 0.99 g (0.004 mole) of crown ether were taken up in 25 ml of trifluoroacetic acid, and 32 ml (0.227 mole) of trifluoroacetic anhydride were added dropwise with stirring at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; copper(I) iodide; In ethyl acetate; N,N-dimethyl-formamide; toluene; | (4) A mixture of 1.00 g of 2,2-bis(fluoromethyl)-6-iodo-2H-1-benzopyran-4-carboxylic acid ethyl ester, 0.84 g of <strong>[2923-16-2]potassium trifluoroacetate</strong>, 1.18 g of cuprous iodide, 4 ml of toluene and 10 ml of N,N-dimethylformamide was stirred with heating under an atmosphere of a nitrogen gas with removing toluene at 150° C. for 5.5 hours. To the reaction mixture was added a mixed solution of 2N hydrochloric acid and ethyl acetate and insolubles were filtered using Celite. An organic layer was separated from the filtrate and a water layer was extracted with ethyl acetate. It was washed together with the obtained organic layer with a saturated saline solution, dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (developing solution, ethyl acetate:hexane =10:1) to obtain 0.51 g of an oily product of 2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxylic acid ethyl ester. NMR (CDCl3)delta: 1.36(3H,t), 4.31(2H,q), 4.53(4H,d), 6.63(1H,s), 6.94(1H,d), 7.47(1H,dd), 8.31(1H,d). MS m/z: 336 (M+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,1'-carbonyldiimidazole; In tetrahydrofuran; tertamethylammonium iodide; | Example 1 A solution of 0.5 g of 2-methyl-4-phenoxy5-trifluoromethylbenzoic acid obtainable by reaction of methyl 2-methyl-4-phenoxy-5-bromobenzoate with <strong>[2923-16-2]potassium trifluoroacetate</strong> in the presence of Cul and tetramethylammonium iodide and subsequent hydrolysis! and 300 mg of carbonyldiimidazole in 15 ml of THF is stirred at room temperature for two hours and then added to 383 mg of guanidine. The mixture is stirred for a further two hours. After customary working up, N-diaminomethylene-2-methyl-4-phenoxy-5-trifluoromethylbenzamide is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
CuI; tertamethylammonium iodide; In methanol; toluene; | Example 2 1.1 g of methyl 3-methylsulfonyl-4-trifluoromethylbenzoate m.p. 146°-147°; obtainable by reaction of methyl 3-methylsulfonyl-4-bromobenzoate with <strong>[2923-16-2]potassium trifluoroacetate</strong> in the presence of CuI and tetramethylammonium iodide in toluene! are added to a solution of 928 mg of guanidine in 15 ml of methanol. The mixture is stirred for 45 minutes at 50° and, after removal of the solvent and customary working up, N-diaminomethylene3-methylsulfonyl-4-trifluoromethylbenzamide, m.p. 233°-234°, is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With hydrogenchloride; In dimethyl sulfoxide; N,N-dimethyl-formamide; | EXAMPLE 1 A mixture of <strong>[2923-16-2]potassium trifluoroacetate</strong> (210 mg, 1.4 mmol and 1,3,5-trinitrobenzene (100 mg, 0.47 mmol) in one mL of N,N-dimethylformamide (DMF) or in one mL of dimethylsulfoxide (DMSO) was heated at 150° C. for one hour. A deep red solution of a Meisenheimer complex of formula (II) above (Z=nitro; Q=trifluoromethyl; R and R'=H; M=K; and n=1) was obtained. The structure of the complex was verified by NMR spectroscopy. Oxidation of a DMF solution of this complex by dropwise addition of tert-butylhypochlorite until the red color disappeared (about seven drops) followed by aqueous workup (10 mL of 1M HCl, extracted with three portions of diethyl ether afforded an oil. This was purified by preparative thin layer chromatography (one 2 mm silica gel plate eluted with 50percent petroleum ether/50percent dichloromethane) to give 53 mg (40percent yield) of 1-trifluoromethyl2,4,6-trinitrobenzene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.8% | With sulfur dioxide; In N,N-dimethyl-formamide; at 100 - 145℃; for 5h; | EXAMPLE 2 (INVENTION) Preparation of Potassium Trifluoromethylsulfinate CF3SO2K by Sulfination of Potassium Trifluoroacetate in the Presence of SO2 According to a Semicontinuous Implementation (0085) The following are introduced at ambient temperature into a 500 ml jacketed reactor equipped with a condenser having an aqueous glycol solution at ?15° C., with a stirrer and with baffles: (0086) 200 g of anhydrous dimethylformamide (DMF) (0087) 50 g of <strong>[2923-16-2]potassium trifluoroacetate</strong> (KTFA), i.e, a KTFA concentration equal to 20 weight percent in the DMF-KTFA mixture. (0088) The reactor is equipped with a Raman probe which makes it possible to monitor, in the medium, the concentration of dissolved SO2; this probe is connected by an optical fiber to the Raman spectrometer. (0089) The medium is stirred and brought to a temperature of 100° C. (0090) Via a dip pipe connected to the SO2 cylinder, an amount of 1.25 g of gaseous SO2 is continuously introduced into the reactor through a micrometric regulating valve, so as to have a concentration of dissolved SO2 equal to 0.5 weight percent and an initial SO2/KTFA molar ratio of 0.059. (0091) The temperature is brought to 145° C. while keeping the SO2 concentration constant at 0.5 weight percent. The reaction is allowed to take place for 5 hours while regulating the SO2 concentration at 0.5 weight percent. (0092) After 5 hours, the reaction mixture is cooled and analyzed by NMR, and the results are as follows: (0093) Degree of conversion of the <strong>[2923-16-2]potassium trifluoroacetate</strong>: 90percent (0094) Yield of potassium trifluoromethylsulfinate: 64.8percent |
52.8% | With sulfur dioxide; In N,N-dimethyl-formamide; at 140℃; for 4.41667h; | EXAMPLE 1Preparation of Potassium Trifluoromethylsulfinate125.5 g of dimethylformamide are charged at ambient temperature (approximately 20° C.) to a 500 cm3 reactor equipped with a jacket, a central mechanical stirrer and an outlet to the atmosphere and an acetone/dry ice condenser which makes possible the reflux of sulfur dioxide.25.5 g of <strong>[2923-16-2]potassium trifluoroacetate</strong> are introduced into the DMF.6.9 g of sulfur dioxide are subsequently charged via a capillary connected to a bottle of sulfur dioxide under pressure.The mixture is heated at 140° C. and at atmospheric pressure.The molar ratio of SO2 to the KTFA is 0.64.After 4 hours 25 min. analysis by ion chromatography gives the following results: Degree of conversion of the potassium 57.1percent trifluoroacetate: Yield of potassium 52.8percent trifluoromethylsulfinate: Selectivity for potassium 92.4percent trifluoromethylsulfinate: A very good reaction selectivity is recorded. |
With sulfur dioxide; N,N-dimethyl-formamide; at 140℃;Autoclave; | Step b: [0356] A solution of TFAK (0.913 kg, i.e. 6 mol) in DMF (5.22 kg) was placed in a prewashed and dried 15 L autoclave. SO2 was then added to the TFAK/DMF solution by sparging, and the exact amount introduced (0.768 kg, i.e. molar SO2/TFAK 2 l) was determined by weighing. The reactor was then closed and heated with stirring at 140° C. for 4 to 5 hours. After returning to room temperature, the reactor was degassed, and its contents were transferred into a 10 L glass vessel. After suitable dilution, ion chromatographic analysis of the reaction mass gave the following results: A solution of TFAK (0.913 kg, i.e. 6 mol) in DMF (5.22 kg) was placed in a prewashed and dried 15 L autoclave. SO2 was then added to the TFAK/DMF solution by sparging, and the exact amount introduced (0.768 kg, i.e. molar SO2/TFAK 2 l) was determined by weighing. The reactor was then closed and heated with stirring at 140° C. for 4 to 5 hours. After returning to room temperature, the reactor was degassed, and its contents were transferred into a 10 L glass vessel. After suitable dilution, ion chromatographic analysis of the reaction mass gave the following results: [0357] Weight balance: 97percent (weight collected: 6.7 kg) [0358] Conversion of the TFAK (molar): 64percent±2.5percent (TFAK assayed in the reaction medium: 0.326 kg) [0359] Yield of TFSK (molar): 50percent±2.5percent (TFSK assayed in the reaction medium: 0.517 kg) The preceding crude reaction product (mixture of TFAK and TFSK) (6.5 kg) was then concentrated under vacuum to give 4.1 kg of DMF, recycled into the following operation, and with a residue (2.02 kg) discharged into the following step. |
With sulfur dioxide; In N,N-dimethyl-formamide; at 140℃;Autoclave; | A solution of KTFA (0.913 kg, 6 mol) in DMF (5,22kg) was introduced into a 15 L autoclave, previously washed and dried.SO2was then added to the KTFA / DMF solution by bubbling, and the exact amount introduced (0,768kg or SO2/ KTFA molar -2 I) was determined by weighing.The reactor was then closed and heated with stirring at 140 ° C for 4 to 5 hours.After returning to room temperature, the reactor was degassed and its content was transferred to a 10L glass recipe.After appropriate dilution, the analysis by ion chromatography of the reaction mass has the following results:? weight balance: 97percent (collected weight: 6,7kg)? Conversion of KTFA (mole): 64percent ± 2.5percent (KTFA assayed in the reaction medium: 0,326kg)? Yield TFSK (mole): 50percent ± 2.5percent (TFSK assayed in the reaction medium: 0,517kg)The crude reaction mixture (mixture of KTFA and TFSK) above (6.5kg) was then concentrated under vacuum to 4.1kg of DMF recycled to the next operation, and a base (2,02kg) drained toward 'next step. | |
64.8%Spectr. | With sulfur dioxide; In N,N-dimethyl-formamide; at 100 - 145℃; for 5h; | The following are introduced at room temperature into a 500 ml jacketed reactor equipped with a condenser having an aqueous glycol solution at ?15° C., with a stirrer and with baffles: (0178) 200 g of anhydrous N,N-dimethylformamide (DMF); (0179) 50 g of <strong>[2923-16-2]potassium trifluoroacetate</strong> (KTFA), i.e. a KTFA concentration equal to 20percent by weight in the DMF-KTFA mixture. (0180) The reactor is equipped with a Raman probe which makes it possible to monitor, in the medium, the concentration of dissolved SO2; this probe is connected by an optical fiber to the Raman spectrometer. (0181) The medium is stirred and brought to a temperature of 100° C. (0182) Via a dip pipe connected to a pressurized sulfur dioxode cylinder, an amount of 1.25 g of gaseous SO2 is continuously introduced into the reactor through a micrometric regulating valve, so as to have a concentration of dissolved SO2 equal to 0.5percent by weight and an initial SO2/KTFA molar ratio of 0.059. (0183) The temperature is brought to 145° C. while keeping the SO2 concentration constant at 0.5percent by weight. The reaction is allowed to take place for 5 hours while regulating the SO2 concentration at 0.5percent by weight. (0184) After 5 hours, the reaction mixture is cooled and analyzed by NMR, and the results are as follows: (0185) Degree of conversion of the <strong>[2923-16-2]potassium trifluoroacetate</strong>: 90percent; (0186) Yield of potassium trifluoromethylsulfinate: 64.8percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With copper(l) iodide; In 1-methyl-pyrrolidin-2-one; at 150℃; for 5h; | To a solution of the product from Step C (8.32 g, 21.8 mmol) in l-methyl-2-pyrrolidone (100 mL) is added <strong>[2923-16-2]potassium trifluoroacetate</strong> (16.6 g, 108.8 mmol) and copper(I) iodide (20.7 g, 108.8 mmol). The reaction is stirred at 150 °C for 5 hours and then is allowed to cool to room temperature. The mixture is partitioned between ethyl acetate and saturated aqueous ammonium chloride and is filtered through Celite, washing the filter cake with ethyl acetate. The layers of the filtrate are separated and the aqueous phase is further extracted with ethyl acetate. The combined organic phases are washed with brine, dried over Na2SO4 and the solvent is removed in vacuo. The crude material is purified via silica gel chromatography using a gradient elution of 0-8percent ethyl acetate/hexanes to afford the desired product as an off-white solid (6.30 g, 89percent). LCMS: 325.20 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Example 14: Potassium salt of trifluoroacetic acid (CF3-COOK (5)); 20 ml water, 73 ml MeCN, 1.33 g KBr, TEMPO (0.46 g), and 10 g of trifluoroethanol are placed in a 500 ml glass flask equipped with a dropping funnel and stirrer. 175ml of 15percent> wt. aq. NaOCl buffered to pH 8-9 were added via the dropping funnel in 3 portions over two days while stirring at room temperature. Concentrated sulphuric acid and water were added to make the reaction mixture acidic (pH 1 to 2). The reaction mixture was extracted three times with diethyl ether. The combined ether phases were dried over magnesium sulphate and then distilled at atmospheric pressure. Methanol (60 ml) and potassium methoxide (7 g) were added to the distillate and the mixture was stirred for one hour at room temperature, filtered and evaporated to give a colorless solid (13.13 g) Yield: 86percent. 19F NMR (D20): -76.82 (s, 3F). | |
86% | With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; In water; acetonitrile; at 20℃;aq. buffer; | General rocedure: 5.5 ml of aq. solutions of KBr (0.55 mol/dm3), 20 ml MeCN, TEMPO (0.12 g, 0.00077 mol), and 2,2,3-trifluoro-3-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-propan-1-ol (2a) (10 g, 0.0275 mol) were placed in the flask. 14percent aq. NaOCl (48 ml) buffered by NaHCO3 (5.2 g) were added via the dropping funnel in 3 portions during two days of stirring in a room temperature (slight exothermic effect). The progress of reaction was monitored by 19F NMR spectroscopy. Then concentrated sulfuric acid followed by water was added. After extraction with diethyl ether, the organic phases were dried over magnesium sulfate. The solvent was evaporated to give a colorless liquid, which was distilled. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; water; at 20℃; | <strong>[2923-16-2]Potassium trifluoroacetate</strong> (9.7 g; 63.8 mmol), tetrabutylammonium bromide (43.4 g; 128 mmol) are charged to a reactor, in the presence of water (75 g) and dichloromethane (65 g).The whole mixture is stirred at ambient temperature and the phases are decanted.The organic phase obtained contains 88percent of the trifluoroacetate anions initially introduced (RR). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; In N,N-dimethyl-formamide; toluene; at 170℃; for 18.75h; | Description 44Methyl 4-methyl-2-(methyloxy)-5-(trifluoromethyl)benzoate (D44)To a mixture of methyl 5-bromo-4-methyl-2-(methyloxy)benzoate (may be prepared as described in Description 43; 2.5 g, 9.65 mmol) in N,N-dimethylformamide (40 ml) was added copper (I) iodide (4.04 g, 21.23 mmol) and <strong>[2923-16-2]potassium trifluoroacetate</strong> (2.94 g, 19.30 mmol). Toluene (10 ml) was added and the mixture heated in Dean Stark apparatus at 170°C for 45 minutes. The toluene was removed via the Dean Stark trap and the resulting mixture was heated for 18 hours at 170°C. The mixture was diluted with water (10 ml) and ethyl acetate (20 ml) and the solid was removed using Celite. The filtrate was taken and the organic layer separated, dried (MgS04) and the solvent removed in vacuo. The residue was purified by column chromatography (Si02, 50percent Cyclohexane/diethyl ether) to yield the title compound as a white solid. 1.76 g.MS (electrospray): m/z [M+H]+ 249 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; In water; at 50℃; under 1.50015 - 10.5011 Torr;Inert atmosphere;Product distribution / selectivity; | EXAMPLE 1; An aqueous solution (774 g) comprising 16percent by weight of potassium trifluoromethanesulfinate and 13.5percent by weight of <strong>[2923-16-2]potassium trifluoroacetate</strong> is charged to a 1 liter jacketed glass reactor equipped with a central stirrer and maintained under a nitrogen atmosphere.The combination is placed under a pressure varying from 14 mbar to 2 mbar while maintaining a temperature of 50° C.225 g of a suspension are obtained, which suspension remains fluid at 50° C.The concentrated solution is run onto concentrated 92percent sulfuric acid (780 g) in a reactor surmounted by a distillation column and by a condenser cooled with water (15° C.)The temperature of the medium is kept below 30° C. during the operation in which the concentrated aqueous solution is run in.The pressure is lowered to 280 mbar and the temperature of the reboiler is maintained at 68° C.During the distillation, the pressure is gradually lowered to 86 mbar in order to maintain a satisfactory flow rate of distillate.The first distillation fraction is collected (56 g) when the temperature of the vapors at the column top is between 26° C. and 36° C.This fraction is composed of 85percent by weight of trifluoroacetic acid and 15percent of triflinic acid.The pressure is subsequently lowered to 3 mbar.A second fraction (44 g) is collected when the temperature of the vapors at the column top is between 29° C. and 41° C.During this operation, the temperature of the reboiler varies from 70° C. to 79° C.This fraction comprises 99percent pure trifluoromethanesulfinic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With copper(l) iodide; In N,N-dimethyl-formamide; toluene; at 160℃; for 4h;Dean-Stark; | To a solution of 25a (619 mg, 1.7 mmol) in DMF/toluene (1:1, 24 mL) were added <strong>[2923-16-2]potassium trifluoroacetate</strong> (1020 mg, 6.7 mmol) and copper(I) iodide (640 mg, 3.4 mmol) at room temperature. The mixture was stirred at 160 °C for 4 h, while water contained in <strong>[2923-16-2]potassium trifluoroacetate</strong> was removed by azeotropy with toluene using Dean?Stark apparatus. The reaction mixture was partitioned between EtOAc (20 mL) and saturated aqueous NaHCO3 (20 mL). After removal of insoluble precipitate by filtration, the aqueous layer of filtrate was extracted with EtOAc (3 × 15 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (15 mL), water (2 × 15 mL) and brine (15 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0?9percent EtOAc in n-hexane) to give 25e (430 mg, 72percent) as yellow oil. MS (ESI+): [M+H]+ 358.1. 1H NMR (300 MHz, CDCl3) delta 1.20 (3H, t, J = 7.2 Hz), 4.16 (2H, q, J = 7.2 Hz), 7.09?7.18 (2H, m), 7.31 (2H, dd, J = 8.7, 4.9 Hz), 7.37 (1H, s), 7.73 (1H, s). |
Tags: 2923-16-2 synthesis path| 2923-16-2 SDS| 2923-16-2 COA| 2923-16-2 purity| 2923-16-2 application| 2923-16-2 NMR| 2923-16-2 COA| 2923-16-2 structure
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