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CAS No. : | 349-76-8 | MDL No. : | MFCD00000391 |
Formula : | C9H7F3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ABXGMGUHGLQMAW-UHFFFAOYSA-N |
M.W : | 188.15 | Pubchem ID : | 67682 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.64 |
TPSA : | 17.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.55 cm/s |
Log Po/w (iLOGP) : | 2.04 |
Log Po/w (XLOGP3) : | 2.67 |
Log Po/w (WLOGP) : | 4.06 |
Log Po/w (MLOGP) : | 2.82 |
Log Po/w (SILICOS-IT) : | 3.18 |
Consensus Log Po/w : | 2.95 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.9 |
Solubility : | 0.238 mg/ml ; 0.00126 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.68 |
Solubility : | 0.393 mg/ml ; 0.00209 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.62 |
Solubility : | 0.045 mg/ml ; 0.000239 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.25 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P210-P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501 | UN#: | N/A |
Hazard Statements: | H227-H315-H319-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 |
---|---|---|
81.7% | With pyridinium perbromide hydrobromide In toluene at 0 - 20℃; for 5 h; | Reference Example 6 Synthesis of 2-bromo-3'-trifluoromethylacetophenone To a toluene solution (423 mL) of commercially available 3'-trifluoromethylacetophenone (79.6 g, 0.423 mol) was added pyridinium bromide perbromide (135.4 g, 0.423 mol) under ice cooling and stirred for 5 hours while heating up to room temperature. The reaction liquid was ice cooled again, followed by dropwise adding 400 mL of distilled water to stop reaction and fractionation. A toluene layer was washed with 400 mL of a saturated aqueous solution of sodium bicarbonate, followed by drying with magnesium sulfate anhydride and concentration under reduced pressure and distillation under reduced pressure to obtain an objective compound (92.35 g, 81.7percent). 1H-NMR (200 MHzFT,TMS,CDCl3) 4.46(2H,s), 7.66(1H,brt,J=7.9Hz), 7.88(1H,brd,J=7.6Hz), 8.19(1H,brd,J=7.5Hz), 8.25(1H,brs) b.p. 92°C /3 mmHg |
78% | With bromine In dichloromethane at 20℃; for 4 h; | EXAMPLE 54; 4-{4-r4-(3-Trifluoromethyl-phenyl)-lH-imidazol-2-yl1-piperidin-l-yl}-lH-pyrazolo- r3,4-(/1pyrimidine hydrochloride; To a 22L 4-necked round bottom flask (fitted with addition funnel, nitrogen blanket, condenser, scrubber and mechanical stirrer) add: 3-trifluoromethyl- acetophenone (1500 g, 1.00 equiv; 7.97 moles) and dichloromethane (7.5L). Stir the resulting clear, colorless solution at room temperature while adding a solution of bromine (127 '4 g; 1.00 equiv; 7.97 moles) in dichloromethane at room temperature via addition funnel over 4 hours. Quench the reaction by slow addition of saturated aqueous NaHCψ3 (2000 mL), controlling the temperature by ice bath to less than 25 0C. Separate the phases and wash the organic layer with saturated aqueous sodium chloride (2000 mL), then dry the solution over sodium sulfate, filter and concentrate to a clear colorless oil. Purify this crude oil by silica gel chromatography (step gradient, 20percent to 50percent CH2Cl2 in heptane) to afford 2-Bromo-l-(3-trifluoromethyl-phenyl)-ethanone (1667g, 6.24 mol, 78percent) as a clear, colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With palladium; hydrogen; In methanol; at 30℃; for 20h; | To a solvent of methanol (2 mL) with a PdNPore (2.7 mg, 5 mol%) catalyst, m-trifluoromethylacetophenone (94.1 mg, 0.5 mmol) was added, and the mixture was placed on a magnetic stirrer and reacted at 30 C for 20 h Column chromatography (silica gel, 200-300 mesh; developing solvent, petroleum ether, ethyl acetate) gave 94.1 mg of 1- (3-trifluoromethylphenyl) ethanol with a yield of 99%. |
88% | With tris(triphenylphosphine)ruthenium(II) chloride; (3aR,5R,7R,7aS)-2-(2-(diphenylphosphino)phenyl)-6,6-dimethyl-3a,4,5,6,7,7a-hexahydro-5,7-methanobenzo[d]oxazole; isopropyl alcohol; sodium hydroxide; for 0.5h;Inert atmosphere; Reflux; | General procedure: In a two-neck flask (25 mL), under an inert atmosphere, wereplaced a catalyst solution (0.05 M in isopropanol, 100 lL, 5 lmol),a degassed 0.125 M solution of sodium hydroxide or potassium tert-butoxide in isopropanol (1 mL, 0.125 mmol), and degassed isopropanol(4 mL). After stirring for 15 min. at room temperature acetophenone (120 mg, 1 mmol) was added and the reaction mixture was refluxed for 30 min. Isopropanol was removed on rotary evaporator and 1-phenylethanol was isolated by flash column chromatography on silica gel (eluent: n-hexane:ethyl acetate80:20). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With [(2-(benzoimidazol-2-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine)RuCl2(PPh3)]; potassium tert-butylate; acetone; In methanol; at 56℃; under 750.075 Torr; for 0.166667h;Inert atmosphere;Catalytic behavior; | General procedure: The catalyst solutionwas prepared by dissolving complex 3(36.1 mg,0.05mmol) in methanol (5.0 mL).Under a nitrogen atmosphere, the mixture of an alcohol substrate (2.0 mmol) and1.0 mL of the catalyst solution (0.01mmol) in 20mL acetone was stirred at 56 Cfor 10 minutes. tBuOK(22.4mg, 0.2 mmol)was then added to initiate the reaction.At the stated time, 0.1 mL of the reaction mixture was sampled and immediately diluted with 0.5 mL acetone pre-cooled-to-0 C for GC or NMR analysis. After the reaction was complete, the reaction mixture was condensed under reduced pressure and subject to purification by flash silica gel column chromatography to afford the corresponding ketone product, which was identified by comparison with the authentic sample through NMR and GC analysis. |
89% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium acetate; (S)-3-phenyl-2-(phenylamino)propionic acid; copper(ll) bromide; In water; for 12h;Reflux; Schlenk technique; | General procedure: A mixture of 1-phenethyl alcohol (1.0 mmol), N-(phenyl)phenylalanine(0.0241 g, 0.1 mmol), CuBr2 (0.0223 g, 0.1 mmol),NaOAc (0.1640 g, 2.0 mmol), TEMPO (0.0156 g, 0.1 mmol), andH2O (3.0 mL) were placed into a 100 mL Schlenk tube, whichwas vigorously stirred in air under reflux for 12 h. After thereaction, the product was extracted with CH2Cl2 (3 × 2.0 mL).The combined organic phase was washed with H2O (3.0 mL) anddried over anhydrous MgSO4. After concentration undervacuum, the residue was purified by column chromatography toafford acetophenone.Isolated yield: 0.1080 g (90%). |
82% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iron(III) trifluoromethanesulfonate; L-phenylalanine; oxygen; In tert-Amyl alcohol; for 60h;Reflux; Green chemistry; | Equipped with a magnetic stirrer in round bottom flask methyl benzyl alcohol (12. 22g, 100. Ommol, namely formula The R1 is 4-methyl, R2 is hydrogen, X is carbon, eta is 1, m is 0), ferric chloride (0. 81g, 5mmol), L- isoleucineAcid (1.31g, 10mmol), TEMP0 (1.56g, 10mmol), toluene 300. OmL was added , then the reaction with oxygen in the air bottleReplacement, stirred and reflux for 6h. After completion of reaction, the reaction mixture was cooled to room temperature, filtered, the filtrate evaporated to give the crude product,The resultant crude product was purified by column chromatography, with n-hexane: Elution: (10 1 volume ratio) mixed liquid of ethyl acetate containing the desired collectionLabeled compound of the eluent, evaporation of the solvent and dried to give the product p-tolualdehyde 10. 93g, 91% yield. 1 - (3-trifluoromethyl phenyl) ethanol (1.90g, 10. Ommol, i.e., of formula (I), R1 is3_ trifluoromethyl methyl, R2 is methyl, X is carbon, [eta] is l, m is 0) is added , experimental methods and procedures were the same as in Example 1, except that:Iron trifluoromethanesulfonate (billion ? 50g, 1. Ommol), L- phenylalanine (0 · 02g, 0. Lmmol), TauEpsilonMuRho0 (0 · 02g, 0. Lmmol),Tert-amyl alcohol 30. OmL, oxygen and the reaction was stirred at reflux after bottle air displacement 60h. The final product was obtained 1. 54g, yield82% |
70% | With tert.-butylhydroperoxide; In water; at 100℃; for 24h; | General procedure: Caution. tert-Butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable, and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. A solution of secondary alcohol (1 mmol) and 70% TBHP (6 or 10 equiv.) was stirred at 100 C for 24 h. The reaction mixture was quenched with the saturated solution of sodium thiosulfate (5 mL) and extracted with dichloromethane (3 x 10 mL). The combined dichloromethane extracts were dried over anhydrous Na2SO4 and filtered, and then the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE or PE/EtOAc as the eluent to obtain the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium acetate; In ethanol; water; for 2h;Reflux; | [1] The 3-trifluoromethyl-acetophenone 0.940g (5.0mmol), methoxy amine hydrochloride 0.835g (10.0mmol), anhydrous sodium acetate 1.640g (20.0mmol), 10ml of ethanol and 30ml water Join 100ml flask.After the reaction mixture was heated to reflux for 2 hours the reaction was monitored by TLC, diluted with 15ml of ethyl acetate, and extracted. The organic phase was dried under reduced pressure to remove the solvent to give 3-trifluoromethyl-acetophenone oxime ether 0.933g (86% yield). |
With pyridine; In ethanol; for 0.75h;Heating / reflux; | Methoxylamine hydrochloride (2.33 g) is added to a solution of 3'-(trifluoromethyl)-acetophenone (1.5 g) in ethanol (20 mL) and pyridine (2 mL). The solution is heated at reflux for 45 minutes. The reaction mixture is then cooled, concentrated under reduced pressure and partitioned between water and ethyl acetate. The aqueous layer is extracted with ethyl acetate. The combined organic layers are washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the desired product as a colorless oil (1.61 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.7% | With pyridinium perbromide hydrobromide; In toluene; at 0 - 20℃; for 5h; | Reference Example 6 Synthesis of 2-bromo-3'-trifluoromethylacetophenone To a toluene solution (423 mL) of commercially available 3'-trifluoromethylacetophenone (79.6 g, 0.423 mol) was added pyridinium bromide perbromide (135.4 g, 0.423 mol) under ice cooling and stirred for 5 hours while heating up to room temperature. The reaction liquid was ice cooled again, followed by dropwise adding 400 mL of distilled water to stop reaction and fractionation. A toluene layer was washed with 400 mL of a saturated aqueous solution of sodium bicarbonate, followed by drying with magnesium sulfate anhydride and concentration under reduced pressure and distillation under reduced pressure to obtain an objective compound (92.35 g, 81.7%). 1H-NMR (200 MHzFT,TMS,CDCl3) 4.46(2H,s), 7.66(1H,brt,J=7.9Hz), 7.88(1H,brd,J=7.6Hz), 8.19(1H,brd,J=7.5Hz), 8.25(1H,brs) b.p. 92C /3 mmHg |
78% | With bromine; In dichloromethane; at 20℃; for 4h; | EXAMPLE 54; 4-{4-r4-(3-Trifluoromethyl-phenyl)-lH-imidazol-2-yl1-piperidin-l-yl}-lH-pyrazolo- r3,4-(/1pyrimidine hydrochloride; To a 22L 4-necked round bottom flask (fitted with addition funnel, nitrogen blanket, condenser, scrubber and mechanical stirrer) add: 3-trifluoromethyl- acetophenone (1500 g, 1.00 equiv; 7.97 moles) and dichloromethane (7.5L). Stir the resulting clear, colorless solution at room temperature while adding a solution of bromine (127 '4 g; 1.00 equiv; 7.97 moles) in dichloromethane at room temperature via addition funnel over 4 hours. Quench the reaction by slow addition of saturated aqueous NaHCtheta3 (2000 mL), controlling the temperature by ice bath to less than 25 0C. Separate the phases and wash the organic layer with saturated aqueous sodium chloride (2000 mL), then dry the solution over sodium sulfate, filter and concentrate to a clear colorless oil. Purify this crude oil by silica gel chromatography (step gradient, 20% to 50% CH2Cl2 in heptane) to afford 2-Bromo-l-(3-trifluoromethyl-phenyl)-ethanone (1667g, 6.24 mol, 78%) as a clear, colorless oil. |
With bromine; In acetic acid; | PREPARATION 1 m-(Trifluoromethyl)phenacyl Bromide m-(Trifluoromethyl)acetophenone (10 g, 0.054 mol) was dissolved in 100 ml acetic acid. Bromine (9.1 g, 0.057 mol) was separately dissolved in 20 ml acetic acid and added portionwise over 0.5 hours to the acetophenone solution. The mixture was stirred for 15 hours, poured onto 150 g ice and extracted with 300 ml ether. The organic layer was washed 1*300 ml H2 O, 1*300 ml saturated NaCl, dried (MgSO4) and evaporated to yield title product as a pale yellow liquid. |
With bromine; In 1,4-dioxane; for 0.166667h; | Example 127 2-Bromo-1-(3-trifluoromethyl)-ethanone To a stirred solution of 1-(3-trifluoromethyl-phenyl)-ethanone (6.15 g, 32.8 mmol) (Aldrich) in dioxane (20 mL) was added dropwise a solution of bromine (5.27 g, 32.9 mmol) in dioxane (60 mL). After addition, the mixture was stirred for 10 minutes, concentrated in vacuo, and the residue chromatographed on silica gel (4:1 hexane/dichloromethane) to provide 2-bromo-1-(3-trifluoromethyl)-ethanone. | |
With bromine; In diethyl ether; at 20℃; for 1h; | Intermediate 3a: 2-bromo-l-('3-(trifluoromethyl phenyl')ethanone. Into a 250-mL round bottom flask, was placed a solution of l-(3-(trifluoromethyl)phenyl)ethanone (5 g, 26.57 mmol, 1.00 equiv) in ether (80 mL). To this was added dropwise a solution of Br2 (4.26 g, 26.66 mmol, 1.00 equiv) in ether (20 mL) with stirring over 1 hr and the resulting solution was stirred an additional 1 h at room temperature. The mixture was washed with 2x30 mL of NaHS03 and 1x30 mL of brine, then dried over anhydrous sodium sulfate and concentrated under vacuum to give 5.2 g (crude) of 2-bromo-l-(3- (trifluoromethyl)phenyl)ethanone as yellow oil. | |
With copper(ll) bromide; In chloroform; ethyl acetate;Reflux; | Example 17; iV-(5-(2-cyanophenoxy)-4-(3-(trifluoromethyl)phenyl)thiazol-2~yI)-2-(4- (ethylsulfonyl)phenyl)acetamide; Step 1:; To a solution of l-(3-(trifluoromethyl)phenyl)ethanone (5 g) in chloroform (30 mL) and ethyl acetate (30 mL) was added copper(II) bromide (7.5 g). The reaction mixture was refluxed overnight. Solvent was removed to give 3-(trifluoromethyl)benzoyl bromide (6 g) as a brown oil. MS(ES+) m/z 253 (MH ). | |
With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 40℃;Darkness; | General procedure: Ketone (1 eq) and N-bromosuccinimide (NBS) (2 eq) were solved in acetonitrile and trimethylsilyl trifluoromethanesulfonate (TMS-OTf) (1 eq) was added. The reactions were stirred at T = 40 C until completeness, diluted with diethyl ether (2 ml), washed with H2O (3 x 2 ml), dried over Na2SO4 and concentrated under reduced pressure. This procedure provided bromoketones intermediates in 75-90% overall yield, with purities generally >90% as determined by HPLC-MS. The compounds was used without further purification. | |
With tetra-N-butylammonium tribromide; In acetonitrile; at 20℃; for 12h; | General procedure: (i) The commercial available 8a-8l (4 mmol, 1.0 equiv.)was respectively dissolved in acetonitrile (50 mL), adding tetrabutylammoniumtribromide(4 mmol, 1.0 equiv.) later. The mixture was stirred overnight under roomtemperature until the solution turned light yellow or colorless. The solventwas removed in vacuo, the residue wasextracted with dichloromethane and washed with water. The organic layers werecombined and concentrated under vacuum to provide the crude products 9a-9l, which using for next step withoutany purification. | |
With bromine; In dichloromethane; | 1- (3- (Trifluoromethyl) phenyl) ethanone (1 g, 5.3 mmol) was dissolved in 10 mL of dichloromethane. Take liquid bromine (280muL, 5.3 mmol) was dissolved in 5 mL of methylene chloride and slowly added dropwise to the supernatant. Fast response, the color of bromine immediately disappeared. After the reaction is complete, wash with saturated brine, wash with saturated sodium carbonate, dry over anhydrous sodium sulfate, concentrate and use directly in the next step. | |
With copper(ll) bromide; In chloroform; ethyl acetate; for 16h;Reflux; | Example 1. Synthesis of 2-(3-(trifluoromethyl)phenyI)imidazo[l,2-a]pyridin-8-amine (14): Step 1) Preparation of2-bromo-l-(3-(trifluoromethyl)phenyl)ethanone (11): A mixture containing l-(3-(trifluoromethyl)phenyl)ethanone (10; 3.0 g, 15.94 mmol) and CuBr2 (5.34 g, 23.94 mmol) in 1:1 EtOAcZCHCl3 (150 mL) was stirred under reflux for 16 h. After filtration, the crude product, 2-bromo-l-(3- (trifluoromethyl)phenyl)ethanone 11, was obtained by concentration as a tan syrup (4.37 g, yield: 72%). This material was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.8% | The flowability of the magnetic force, thermometer, condenser 100 ml in four-mouth bottle, nitrogen three times, then adding 18.1g (0.1mol) toluene clorotriflouoroethylene between (I), at room temperature, dropping 2.5mol/L (0.1mol) tetrahydrofuran solution of isopropyl magnesium chloride 40.0 ml, 30 minutes the drop finishes. Heating to reflux (70 C) and heat-insulation 3 hours between toluene clorotriflouoroethylene area to be raw material content of less than 5% (GC detection). At this moment benzotrifluoride area content is 89.3%.with acetic anhydride as raw material[072] In a magnetic stirrer,thermometer,In the 1 OOmL four-necked flask,12.2 g (0.12 mol 1) of acetic anhydride was added and the nitrogen was replaced.The above prepared Grignard IV was cooled to 0 C,Then at 0 ~ 5 C,Slowly added to the above acetic anhydride.While maintaining this temperature, stirring was continued for 2 hours,And then heated to 40 C for 1 hour until GC was tested for Grignard IV,At this point the water quenching,Static stratification,Extraction (benzene,Ethyl acetate or dichloromethane),Combine organic phase,Washed to neutral,Desolvation and easy recovery,Distillation A fraction of 119 to 12 l C / 6.67 kPa was collected to give 13.9 g,Yield 73.8%, purity greater than 98%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With aluminium(III) triflate; (carbonyl)chloro(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; hydrogen; 1,2-bis-(diphenylphosphino)ethane; at 140℃; for 16h;Autoclave; | Isolated yields (isolated from the reaction mixture by column chromatography). Examples 17-29 show that various carbonyl compounds can be converted to the corresponding primary amines in good yields using the inventive method. |
50% | Into a 150 mL 3-necked round bottom flask, was placed ethanol (25 mL). NH3 gas was added at 0 C. The mixture was stirred for 1 h at 0 C. Into a 150-mL sealed tube, was placed a solution of 1-(3-(trifluoromethyl)phenyl)ethanone (2 g, 10.64 mmol, 1.00 equiv) in ethanol (5 mL), and Ti[OCH(CH3)2]4 (6.04 g, 21.13 mmol, 2.00 equiv). This was followed by the addition of the above solution of NH3 (gas) in ethanol (25 mL). The mixture was stirred overnight at 48 C. To this was added NaBH4 (600 mg, 15.79 mmol, 1.48 equiv). The resulting solution was stirred for 3 h at room temperature. The resulting solution was diluted with 10 mL of ammonia and the solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane/methanol (50:1). The product was obtained as 1 g (50%) of a yellow oil. | |
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; ammonium formate; In methanol; at 70℃; for 7h;Inert atmosphere; | General procedure: The corresponding ketone (20 mmol, 1.0 eq) and CH3OH (20 mL) were added to a 250 mL Schlenk tube containing [RhCp*Cl2]2 (61.8 mg, 100 mumol, 0.005 equiv) and HCOONH4 (6.36 g, 100 mmol, 5.0eq). The brown mixture was frozen, and the whole system was evacuated. The system was closed and then stirred at 70 C for 7 h. After the dark green resulting solution was cooled to room temperature, 1M aqueous HCl solution (38.4 mL) was added, and the mixture was washed twice with CH2Cl2 (5 mL) to remove the neutral compounds. After addition of a cold 12 M aqueous NaOH solution (3.6 mL) to the aqueous layer, the mixture was extracted six times with CH2Cl2 (12 mL). The combined organic layers were dried over anhydrous Na2SO4. Filtration and evaporation under reduced pressure gave crude amine,which was used without purification. All the crude corresponding amine was dissolved in dichloromethane (50 mL), and TCCA (trichloroisocyanuric acid) (3.2 g, 14 mmol) was added in a250 ml round-bottom flask at 0 C. Then, the mixture was stirred at ambient temperature during 1 h. Triethylamine (6.0 g, 6 mol) dissolved in dichloromethane (50 mL) was added, and the resulting mixture was washed with water (200 mL) and hydrochloric acid (1 M, 200 mL)successively. The organic layer was dried over anhydrous sodium sulfate. After concentration under reduced pressure, purification by column chromatography on silica gel (n-hexane/EtOAc:40/1) afforded pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With D-glucose; In aq. phosphate buffer; at 25℃; for 24h;pH 7.0; | General procedure: For isolation and characterization of the bioreduction product, the reaction was performedon a preparative scale: 300 g resting cells of R. rubra AS 2.2241 were resuspended in 1000 mL of Na2HPO4-KH2PO4 buffer (100 mM, pH 7.0) with 50 g glucose and 10 mM of each substrate (1a-1i,1m and 1n). The reaction mixture was incubated at 25C and shaken at 220 rpm for 24 h. The cellswere removed by centrifugation and the supernatant was saturated with NaCl. The supernatantwas extracted with EtOAc (1000 mL 3). The organic phases were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography onsilica gel (eluent: EtOAc/PE 1:20) to give the enantiomerically pure alcohols 2a-2i, 2m, 2n. The isolatedyield and ee of preparative-scale are comparable to those obtained from screening biotransformations.The spectroscopic data (1H and 13 C NMR, and HPLC retention times) of enantiomerically alcohols 2a-2i, 2m and 2n are in agreement with those obtained for racemic forms, as described in theSupplementary Materials. |
92% | With dimethylsulfide borane complex; (1R,2S,3R,5R)-2-(1',3',2'-dioxaborolan-2'-yloxy)apopinan-3-amine; In tetrahydrofuran; at 20℃; for 1h; | General procedure: To a solution of 1 (0.005-0.01 mmol, 0.5-1 mol %) in dry THF(3 mL) at room temperature, a solution of BH3SMe2 (10 M,100 lL, 1 mmol) in THF (2 mL) was added dropwise at a rate of3.2 mL per hour using a syringe pump. At the same time a solutionof ketone (1 mmol) in THF (2 mL) was also added to the reactionflask at a rate of 3 mL per hour. After the addition of both reagents,the reaction mixture was stirred for 20 min, quenched by the additionof MeOH (1 mL) at room temperature, and stirred for 30 min. Subsequently, the solvents were evaporated under vacuum and theproduct was isolated by column chromatography using hexane/EtOAc (4:1) as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With silver; potassium hydroxide; In toluene; at 80℃; for 24h; | General procedure: To a solution of compound 2-aminobenzyl alcohol (250 mg, 1eq) in Toluene (5 ml) was added acetyl derivatives (1.5 eq) followed by addition of potassium hydroxide (2 eq) and Ag nanoparticles (0.05 eq). Whole reaction mass was heated at 80 C for 24 h. Progress of the reaction was monitored by TLC. After completion of the reaction, as confirmed by TLC, the reaction mass was brought to room temperature and quenched with water. Ethyl acetate/water work up was done. Organic layer was separated and the aqueous layer was once again extracted with ethyl acetate. All the organic layers were combinedand dried over Na2SO4 and concentrated under reduced pressure to obtain crude material, which was purified by column chromatography to obtain desired material using ethyl acetate/hexane as a mobile phase. Formation of the desired product was confirmed by 1H NMR, 13C NMR, and electron ionization mass spectra. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium hydroxide In ethanol; water at 20℃; | General procedure for synthesis of chalcones via Claisen-Schmidt condensation General procedure: To a solution of 2,4,5-trimethoxy benzaldehyde (4mmol) and appropriate acetophenone (4mmol) in C2H5OH (25ml), 40% of aqueous KOH (2mmol) was added. The reaction mixture was stirred at r.t. till completion of reaction (monitored by TLC). Then the reaction mass was poured into ice water and neutralized with aqueous 10% HCl solution. The precipitate was filtered, washed with excess of water, dried and recrystallized from methanol to obtain pure chalcones. |
62% | With sodium hydroxide In methanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Diethyl amine; zinc(II) chloride In <i>tert</i>-butyl alcohol; benzene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.5% | With hydroxylamine hydrochloride; sodium hydroxide; In ethanol;pH 8.0;Reflux; | 1.000 g (5.0 mmol) of trifluoromethylacetophenone,0.5 g (7.0 mmol) of hydroxylamine hydrochloride,10mL of ethanol,Add 0.350g (8.8mmol) sodium hydroxide to adjust pH 8.0,Reflux for 1.0h,Pour into ice water,Hydrochloric acid adjusted to pH 2.0,Precipitating a large amount of white solidBody, suction filtration, washing and drying,Got 0.965gTrifluoromethylacetophenone oxime, white solidThe yield was 95.5%. |
93.5% | With hydroxylamine hydrochloride; sodium hydroxide; In methanol; water; at 25℃; for 4h; | In a 250 mL reaction flask, 3-trifluoromethylacetophenone (10.0 g, 53.1 mmol), hydroxylamine hydrochloride (5.5 g, 79.7 mmol), and methanol 80 mL were added, and then a 20% aqueous sodium hydroxide solution (15.9 g, 79.7) was added dropwise. mmol), and reacted at 25 C for 4 hours. After the reaction, the solvent was distilled off under reduced pressure, washed with water, filtered with suction, and dried to obtain 10.1 g of 3-trifluoromethylacetophenone oxime as a white solid with a yield of 93.5%. |
87% | With hydroxylamine hydrochloride; sodium hydroxide; In methanol; water; at 20℃; for 11h; | 3-Trifluoromethylacetophenone (100.0 g) was dissolved in methanol (500.0 ml). To the solution was added hydroxylamine hydrochloride (37.0 g) at room temperature. To the reaction mass was added solution of sodium hydroxide (32.0 g) in water (150.0 ml) slowly over a period of 1.0 hr at room temperature and stirred for 10.0 hrs. Methanol was distilled off to obtain gummy product which was dissolved in ethyl acetate (500.0 ml). The solution was washed with water (150.0 ml). Organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford l-(3-trifluoromethylphenyl) ethanone oxime (Intermediate-II) as a white solid (94.5 g, 87%) having purity more than 98%. |
With hydroxylamine hydrochloride; sodium acetate trihydrate; In methanol; water; | [1] 7.5 g of 3'-trifluoromethylacetophenone, 6.25 g of hydroxylamine hydrochloride, and 8.8 g of sodium acetate trihydrate were heated in 125 ml of methanol under reflux for one hour. After completion of the reaction, the methanol was distilled off under reduced pressure. 190 ml of water was added to the resulting residue, followed by extraction with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and stripped of the solvent by distillation under reduced pressure to obtain 7.3 g of 3'-trifluoromethylacetophenone oxime having a melting point of 63 to 65 C. | |
With hydroxyammonium sulfate; Bis(2-ethylhexyl)phosphoric acid; In water; methyl cyclohexane; at 70℃; for 0.5h; | General procedure: 50 g of methylcyclohexane, 75.1 g of a 40% aqueous solution of hydroxylammonium sulphate (0.183 mol based on the molecular weight 164.14) and 0.6 g (0.002 mol) of di(2-ethylhexyl)phosphoric acid (95%) were charged in a 250 ml glass reactor equipped with heating jacket, stirrer and reflux condenser and the mixture was heated to 70 C. At this temperature under vigorous stirring, 47 g (0.33 mol) of 4-methylacetophenone (95%) over a period of 30 minutes, and subsequently 43.7 g (0.35 mol) of aqueous sodium hydroxide solution (32%) over a period of 20 minutes, were uniformly added using metering pumps. The pH after completion of the addition of the aqueous sodium hydroxide solution was 6.5. The reaction mixture was further stirred at 70 C. for 60 minutes. The stirrer was then stopped and the organic phase was separated and analyzed by HPLC (Column: Kinetex 2.6 u C18 100 A, 50 C., H2O/CH3CN, 220 nm). Result: 4-Methylacetophenone: 0.2% (HPLC peak area) 4-Methylacetophenone oxime, sum of E and Z isomers: 98.8% (HPLC peak area) The proportion of reactant and product in the aqueous phase is negligible.Performed as in Example 1 with the difference that3 -trifluoromethylacetophenone was used.Result with di(2-ethylhexyl)phosphoric acid:3-Trifluoromethylacetophenone: 0.2% (HPLC peak area)3-Trifluoromethylacetophenone oxime: 99.8% (HPLC peak area) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridinium bromide perbromide, HBr / acetic acid / 0.5 h / Ambient temperature 2: ethanol / 0.5 h / Heating | ||
Multi-step reaction with 2 steps 1: tetra-N-butylammonium tribromide / acetonitrile / 12 h / 20 °C 2: ethanol / 3 h / Reflux | ||
Multi-step reaction with 2 steps 1: copper(ll) bromide / chloroform; ethyl acetate / Reflux 2: ethanol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.5135 g / p-toluenesulfonic acid / toluene / 44 h / Heating 2: 0.72 percent / tetrahydrofuran / 16 h / 23 °C 3: acetic acid / 19 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Example P1; Preparation of 4-(2, 2-dichlorovinyl)-1-(2 4-difluorophenyl)-3-(3-trifluoro- methylphenyl)-1 H-pyrazole (3); Step 1; Preparation of N- (2, 4-difluorophenyl)-N'- [1- (3-trifluoromethylphenyl)-ethylidene]- hydrazine (1); A few drops of glacial acetic acid and 9.47 g of 3-trifluoromethylacetophenone are added dropwise to a solution of 10 g of 2, 4-difluorophenylhydrazine hydrochloride in 50 mi of ethanol. The reaction mixture is heated to reflux and, with the addition of small portions of hydrazine, stirred until the reaction is complete (TLC monitoring). The reaction mixture is concentrated by evaporation, discharged into 2N NaOH and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with water and saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated by evaporation. The residue is filtered over silica gel with ethyl acetate/hexane 5: 95 and the product is crystallised from hexane. 10.64 g (67% of theory) of the hydrazone (1) are obtain- ed in the form of a solid having a melting point of 77-79C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium carbonate; hydrazine hydrate In tetrahydrofuran; ethanol; water; ethyl acetate | 80.A Step A]: 5-Methyl-3-(3-trifluoromethyl-phenyl)-1H-pyrazole Step A]: 5-Methyl-3-(3-trifluoromethyl-phenyl)-1H-pyrazole Ethyl acetate (2.45 ml) was added to THF (50 ml) and treated with sodium hydride (1.09 g, 60% dispersion in oil) under argon. A catalytic amount of ethanol (2 drops) was added followed by dibenzo-18-crown-6 (90 mg) and 3-trifluoromethylacetophenone (2.35 g) dissolved in THF (20 ml)) added over a period of 20 min. The brown mixture was heated to reflux for 2 hours) cooled and poured into water. The pH was adjusted to 5 to 6 with 2N HCl and 2N Na2CO3, respectively. The aqueous phase was extracted with ethyl acetate and the organic layer was washed with brine, dried and evaporated to give the intermediate 1,3-dicarbonyl compound as an orange solid. This material was dissolved in ethanol/water 1:1 (50 ml) and treated with hydrazine monohydrate (0.8 ml). The mixture was refluxed for 3 hours, cooled and poured into water. The pH was adjusted to 8-9 with Na2CO3 solution (2M) and the aqueous layer was then extracted with ethyl acetate. The organic layers were washed with brine, dried and evaporated to give a crude oil. This was purified by flash chromatography (gradient of hexanes in ethyl acetate) to give the title compound as a light yellow solid (1.4 g). MS (ISP): 227.2 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In ethanol; water; for 0.0833333h;Microwave irradiation;Product distribution / selectivity; | Method B; (R)-(I -naphthyl)ethylamine hydrochloride (III) (1.5 g), paraformaldehyde (0.3 g), 3-(trifluoromethyl)acetophenone (II) (1.8 g), 30% w/w aqueous hydrochloric acid (0.1 g), ethanol (4.5 g) and water (1.5 g) were charged into the reactor under stirring and reacted for 5 minutes under microwave irradiation (max 250W), until satisfactory conversion was observed via HPLC. Then water (10.0 g) and toluene (3.0 g) were added and the resulting suspension was stirred at 25C. The title compound (1.6 g) was isolated upon filtration at room temperature, washing with water and methyl 2- propanol and exsiccation at 500C. | |
With hydrogenchloride; In ethanol; water; for 14h;Reflux;Product distribution / selectivity; | (R)-(I -naphthyl)ethylamine hydrochloride (III) (100.0 g), paraformaldehyde (15.9 g), 3-(trifluoromethyl)acetophenone (II) (135.7 g), 30% w/w aqueous hydrochloric acid(5.6 g), ethanol (150.0 g) and water (10.0 g) were charged into the reactor and stirred at reflux for 14 hrs, until satisfactory conversion was observed via HPLC. Then water (300.0 g) and toluene (305.0 g) were added and the mixture was stirred at 25C.The organic and aqueous layers were separated and additional water (200.0 g) was charged over the organic phase in order to favour the precipitation. The title compound (95.6 g) was isolated upon filtration at room temperature, washing with water and methyl tert-butyl ether and exsiccation at 500C. | |
hydrogenchloride; In ethanol; water; for 0.0833333h;microwave irradiation;Product distribution / selectivity; | Method B(R)-(1-naphthyl)ethylamine hydrochloride (1.5 g), paraformaldehyde (0.3 g), 3- (trifiuoromethyl)acetophenone (1.8 g), 30% w/w aqueous hydrochloric acid (0.1 g), ethanol (4.5 g) and water (1.5 g) were charged into the reactor under stirring and reacted for 5 minutes under microwave irradiation (max 250W), until satisfactory conversion was observed via HPLC. Then water (10.0 g) and toluene (3.0 g) were added and the resulting suspension was stirred at 25C. The title compound (1.6 g) was isolated upon filtration at room temperature, washing with water and methyl 2- propanol and exsiccation at 50C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium formate;Cp*IrCl[(S,S)-(C2H5)2CHCH2SO2dpen]; tetrabutylammomium bromide; In water; at 50℃; for 24h;Inert atmosphere; | The reaction was carried out with the same conditions as in Comparative example E-9, except that 0.72 mg (1.0 mumol) of Cp*IrCl[(S,S)-(C2H5)2CHCH2SO2dpen] was used as the catalyst. GC analysis of the reaction product confirmed that 1-(3'-trifluoromethylphenyl)ethanol with 94.3% ee optical purity was produced at 100% yield. Comparison with Comparative example E-9 indicated the superiority of this complex. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: hydrogenchloride / ethanol; water / 0.08 h / microwave irradiation 2.1: sodium hydroxide; sodium tetrahydroborate / water; methanol / 0.5 h / -10 - 0 °C 2.2: 5 - 50 °C / pH 1 3.1: thionyl chloride / toluene / 30 - 40 °C 4.1: sodium hydrogencarbonate / toluene; water / 15 - 20 °C / pH 8 - 9 / Inert atmosphere 4.2: 20 °C / 750.08 Torr | ||
Multi-step reaction with 4 steps 1.1: hydrogenchloride / ethanol; water / 0.08 h / microwave irradiation 2.1: sodium hydroxide; sodium tetrahydroborate / water; methanol / 0.5 h / -10 - 0 °C 2.3: pH 12 - 13 3.1: thionyl chloride / toluene / 5 h / 20 - 30 °C 4.1: sodium hydrogencarbonate / toluene; water / 15 - 20 °C / pH 8 - 9 / Inert atmosphere 4.2: 20 °C / 750.08 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ammonia; ammonium chloride / ethanol; water / 20 h / 70 °C / Autoclave 2: hydrogenchloride; water / 20 °C / Cooling with ice | ||
Multi-step reaction with 2 steps 1: ammonium chloride; ammonium hydroxide / ethanol; water / 20 h / 70 °C / Autoclave 2: water; hydrogenchloride / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; titanium tetrachloride In dichloromethane at 0℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With bromine In dichloromethane at 20℃; for 4h; Inert atmosphere; Large scale reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With copper(l) iodide; 1,10-Phenanthroline; sodium t-butanolate In toluene at 20℃; for 4.5h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With iodine at 100℃; for 8h; | General procedure for synthesis of 2-amino-4-(substituted-phenyl)-1,3-thiazoles General procedure: A mixture of thiourea (7, 50 mmol), the corresponding acetophenone (6, 25 mmol) and iodine(25 mmol) is stirred at 100 °C for 8 h. Then the reaction mixture is cooled, extracted with diethylether to remove excess of acetophenone, and then washed with aqueous sodium thiosulfate to remove excess iodine and later with cold water. The crude product is dissolved in hot water, filtered to remove sulphone, and the filtrate is basified with aqueous Na2CO3 to yield the corresponding 2-amino-4-(substituted-phenyl)-1,3-thiazole (5). The crude product is purified by recrystallization from alcohol. The synthesis and spectral data of compounds 5a-i have been reported by us earlier [2]. The data in respect of compounds 5j-l is described here. |
33% | With iron(III) chloride hexahydrate; iodine at 110℃; for 24h; Sealed tube; Green chemistry; | |
0.85 mg | With carbon tetrabromide; triethylamine In acetonitrile at 20℃; for 3h; | 34.1 Step 1: Synthesis of 4-(3-trifluoromethyl-phenyl)-thiazole-2-amine Trifluoroacetophenone (1.0g, 5.3mmol), thiourea(0.8g, 10.6mmol), triethylamine (2.1g, 21.2mmol), and carbon tetrabromide (7.0g, 21.2mmol) were dissolved in anhydrous acetonitrile (20.0mL). The mixture was reacted at room temperature for 3 h. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic phases were combined, washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated under reduced pressure to remove the solvent to produce a crude product. The crude product was purified with silica gel column chromatography to produce the title compound (0.85g). ESI-MS (m/z): 245.2 [M + H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | General procedure: A 50 mL flask was charged with substituted acetophenone (5 mmol) and a solution of sodium hydroxide (10 mmol) in a 4:1 (v/v) mixture of ethanol/H2O (25 mL), and the resulting mixture was stirred at room temperature for 5 min. A substituted benzaldehyde (5 mmol) was then added to the reaction, and the resulting mixture was stirred at room temperature. The reaction was then monitored byTLC using ethyl acetate/petroleum ether (1:4 or 1:2 v/v) as the solvent system. Upon completion of the reaction, the crude product was filtered off and recrystallized from a mixture of dichloromethane and ethanol or purified by column chromatography over silica gel eluting with a mixture of petroleum ether and ethyl acetate to give the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With methanesulfonic acid; tetrabutylammoniun azide In 1,2-dimethoxyethane at 80℃; for 0.0833333h; Flow reactor; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With sodium hydroxide; In ethanol; water; at 0 - 20℃; | General procedure: Chalcones were prepared utilizing Claisen-Schmidt condensation. To a stirred solution of the substituted acetophenone (1mmol) and the substituted benzaldehyde (1mmol) in ethanol at 0C, sodium hydroxide solution (0.5ml, 50%) was added dropwise. The solution was then stirred at room temperature overnight. The formed precipitate was filtered and washed with cold water and recrystallized from ethanol, to afford chalcones 1-10. Deep yellow solid, yield=45%, m.p.=102-105C, 1H NMR (400MHz, DMSO-d6) delta 8.36 (d, J=7.8Hz, 1H, H4), 8.31 (s, 1H, H2), 8.03 (d, J=7.8Hz, 1H, H6), 7.90 (d, J=15.7Hz, 1H, beta-Olefinic), 7.82 (dd, J=7.8Hz, 1H, H5), 7.74 (d, J=15.7Hz, 1H, alpha-Olefinic), 7.40 (d, J=8.0Hz, 1H, H6?), 7.01 (d, J=7.5Hz, 1H, H4?), 6.92 (dd, J=7.9Hz, 1H, H5?), 6.18 (s, 2H, -O-CH2-O-). 13C NMR (101MHz, DMSO-d6) delta 188.07, 147.69, 146.96, 138.46, 138.14, 132.34, 130.22, 129.52, 124.65, 122.93, 121.95, 121.86, 116.86, 110.39, 101.78. Anal. calcd. for C17H11F3O3: C, 63.76; H, 3.46. Found: C, 63.74; H, 3.41. EI-MS (m/z): calculated 320.1, observed 320.1 (M) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | General procedure: An over-dried 50 mL Schlenk tube equipped with a magnetic stir bar was charged with CuTC (95.3 mg, 0.5 mmol, 1.0 eq) and TBAT (809.8 mg, 1.5 mmol, 3.0 eq). The seal tube was evacuated and backfilled with N2. Then HCF2OTf (233 μL, 2.0 mmol, 4.0 eq) and DMF (10.0 mL) were added by syringes. The mixture was stirred at room temperature for 5 min and diaryliodonium salt (0.5 mmol, 1.0 eq) was added under N2. After stirring for 5 min, the reaction was quenched by H2O and the aqueous layer was extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced vacuum. The resulting residue was purified by column chromatography or HPLC to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With caesium carbonate; In dimethyl amine; at 20℃;Glovebox; | In the glove box,Cs2CO3 (0.6 mmol) and 3-trifluoromethylacetophenone (0.2 mmol) were weighed into a 25 mL reaction tube,Measure the amount of DMA (1 mL) into the reaction tube.A bromodifluoromethylphosphonium salt (0.6 mmol) was weighed,Treated with DMA (2 mL)Inhalation into the syringe.Stirred at room temperature,A DMA solution of bromodifluoromethylphosphonium salt was injected into the reaction tube at a rate of 0.5 mL / h with a syringe pump.After the injection, the reaction is over. The solution in the reaction tube was transferred to a separatory funnel, 15 mL of water was added, extracted three times with dichloromethane (10 mL x 3), and the organic phases were combined and washed three times with water (10 mL x 3). The resulting organic phase was dried over anhydrous sodium sulfate, the solid was filtered off, the solvent was removed, the silica gel column was removed, and the final difluoromethylated product was isolated by using n-pentane and ethyl acetate as eluant. 50%, purity> 99.9% (nuclear magnetic purity). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: 3'-(trifluoromethyl)acetophenone With pyridine; disulfur dichloride In chlorobenzene at 20℃; for 2h; Stage #2: With sulfuryl dichloride In chlorobenzene at 20 - 132℃; for 15.5h; | 14 Example 14: 3-(Trifluoromethyl)benzoyl chloride To a mixture of 3'-(trifluoromethyl)acetophenone (0.152 ml, 1.0 mmol), pyridine (0.012 ml, 0.15 mmol), and chlorobenzene (0.35 ml) was added S2C12 (0.16 ml, 2.0 mmol) while stirring at room temperature. After 2 h S02C12 (0.121 ml, 1.5 mmol) was added dropwise, and the resulting mixture was stirred at room temperature for 0.5 h. The mixture was then stirred at 132 °C for 15 h. The mixture was diluted with CDCI3 (2 ml), an internal standard was added (1BU3PO4, 0.0552 ml, 0.20 mmol), and the mixture was analyzed. 1H NMR indicated that 3-(trifluoromethyl)benzoyl chloride had been formed in 87% yield. 1H NMR (PhCl, CDCI3, 400 MHz) delta = 8.29 (s, 1H), 8.19 (d, J = 8 Hz, 1H), 7.83 (d, J = 8 Hz, 1H), 7.55 (t, J = 8 Hz, 1H). |
76 %Spectr. | With pyridine; disulfur dichloride at 137℃; for 20h; | 5 Example 5: 3-(trifluoromethyl)benzoyl chloride A mixture of 3-(trifluoromethyl)acetophenone (0.188 g, 1.0 mmol), pyridine (0.008 ml, 0.1 mmol), and disulfur dichloride (0.240 ml, 3.0 mmol) was stirred at 137 °C for 20 h. Themixture was diluted with CDC13 (2 ml), an internal standard was added (iBu3PO4, 0.0552 ml,0.20 mmol), and the mixture was analyzed. 1H NMR indicated that3-(trifluoromethyl)benzoyl chloride (76% yield) had been formed.1H NMR (CDC13, 400 MHz) delta = 8.37 (s, 1H), 8.32 (d, J = 8 Hz, 1H), 7.96 (d, J = 8 Hz,1H), 7.71 (t, J = 8 Hz, 1H).13C NMR (CDC13, 100 MHz) delta = 167.2, 134.2, 134.0, 131.74 (quartett, J = 32 Hz), 131.6 (quartett, J = 3 Hz), 129.8, 127.9 (quartett, J = 3 Hz), 123.1 (quartett, J = 270 Hz, CF3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium acetate / ethanol; water / 2 h / Reflux 2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-fluorobis(benzenesulfon)imide; potassium nitrate / nitromethane / 24 h / 70 °C 3: hydrogenchloride; water / diethyl ether / 30 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydrogenchloride In ethanol; water at 80℃; | 3.1 (1) Preparation of intermediate (R) -3- (1- (naphthalen- 1 -yl) ethylamino) -1- (3- (trifluoromethyl) phenyl) 113.0 g (0.6 mol) of m-trifluoromethyl acetophenone,Formaldehyde 27.0 g (0.9 mol) and(R) -1- (1-naphthyl) ethylamine 85.6 g (0.5 mol)Add 300ml of anhydrous ethanol dissolved in stirring,Then, 4.2 ml (0.050 mol) of concentrated hydrochloric acid was added,The reaction was stirred at 80 ° C, the reaction was monitored by TLC,Until (R) -1- (1-naphthyl) ethylamine disappears and the reaction is stopped;The reaction solution was added dropwise 10% sodium hydroxide solution stopped reaction to adjust the pH to 10,And then at 70 under the conditions of the reaction solution was concentrated until no droplets outflow,Stop concentrating200ml of purified water was added to the concentrated residue,Ethyl acetate 400ml, stirred for 30min, then allowed to stand for 15min,Liquid separation, the organic phase was collected,The aqueous phase was washed with 400 ml of ethyl acetate, allowed to stand still,The second liquid separation, the combined organic phase,The organic phase was dried over anhydrous sodium sulfate 100g 5h, filtered,The filtrate was concentrated to solventless effluent,152.1 g of a yellow oil was obtained,The yield was 82.0% for the intermediate (R) -3- (1- (naphthalen-1-yl) ethylamino) -1- (3- (trifluoromethyl) phenyl) ; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With 4-methyl-morpholine; iodine In dimethyl sulfoxide at 120℃; for 16h; | Synthesis of acetophenone derivatives (2a-q) General procedure: A 10 mL reaction flask was charged with terminal alkynes 1a-q (1.0 mmol), I2 (0.3 mmol) and N-methyl morpholine (1.0 mmol) in DMSO (2.0 mL) and then the reaction mixture was heated at 120 °C for 16 h. After completion of the reaction (progress was monitored by TLC; SiO2, hexane/EtOAc = 9:1), the recation mixture was quenched with saturated sodium thiosulphate solution, diluted with water (20 mL) and extracted with ethyl acetate (3 × 15 mL). The combined organic layer was dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and the remaining residue was purified over silica gel column chromatography using hexane/EtOAc = 4:1 as an eluent to obtain the desired products 2a-q in high yields. |
72% | With 4-methyl-morpholine; iodine; dimethyl sulfoxide at 120℃; for 16h; | Synthesis of acetophenone derivatives (2a-q) General procedure: A 10 mL reaction flask was charged with terminal alkynes 1a-q (1.0 mmol), I2 (0.3 mmol) and N-methyl morpholine (1.0 mmol) in DMSO (2.0 mL) and then the reaction mixture was heated at 120 °C for 16 h. After completion of the reaction (progress was monitored by TLC; SiO2, hexane/EtOAc = 9:1), the recation mixture was quenched with saturated sodium thiosulphate solution, diluted with water (20 mL) and extracted with ethyl acetate (3 × 15 mL). The combined organic layer was dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and the remaining residue was purified over silica gel column chromatography using hexane/EtOAc = 4:1 as an eluent to obtain the desired products 2a-q in high yields. |
57 %Chromat. | With gold(III) trichloride; lithium hydroxide monohydrate In isopropanol at 65℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53 %Spectr. | With 3-methylpyridin-2-ylamine; chlorobis(ethylene)rhodium(I) dimer; ethyl crotonate; 1,3-bis(2,4,6-trimethylphenyl)4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene; water; toluene-4-sulfonic acid In 2-methyltetrahydrofuran at 150℃; for 120h; Inert atmosphere; Glovebox; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With iodine; toluene-4-sulfonic acid hydrazide; In dimethyl sulfoxide; at 100℃; for 6h; | To a dimethylsulfoxide (4 mL) solution of 3'-(trifluoromethyl)acetophenone (400 mg, 2.1 mmol), 2-ethylsulfanylaniline (390.9 mg, 2.6 mmol), 4-methylbenzene sulfonhydrazide (593.9 mg, 3.2 mmol), and iodine (809.4 mg, 3.2 mmol) were sequentially added, followed by stirring at 100 C. for 6 hours. Water was poured in the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with an aqueous 10% sodium thiosulfate solution and then with saturated brine, dried over sodium sulfate, filtered to remove the white precipitate, and concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1:6) to afford the title compound (yielded 315.5 mg, yield: 42%) as a tan oily product. 1HNMR Spectrum (CDCl3) sigma: 8.24 (1H, s), 8.18 (1H, s), 8.14 (1H, d, J=7.3 Hz), 7.64-7.59 (2H, m), 7.55-7.47 (3H, m), 7.39 (1H, td, J1=7.4 Hz, J2=1.5 Hz), 2.83 (2H, q, J=7.3 Hz), 1.24 (3H, t, J=7.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 60% 2: 16% | With iron(III) chloride; palladium diacetate; copper(II) acetate monohydrate; DavePhos In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 40h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.3% | With acetic anhydride In tetrahydrofuran; toluene at -15 - 20℃; for 2h; Inert atmosphere; | 1; 1; 2; 3; 2 Example 1 75.0 g of tetrahydrofuran (1.04 mol; manufactured by nacalai tesque),5.1 g (0.208 mol; made by Chuo Industry Co., Ltd.) of magnesium powder,Charge 8.5 g (0.2 mol; nacalai tesque) of LiCl into a four-necked flask (200 ml) equipped with a thermometer.The system was stirred while replacing the inside with nitrogen.1 mol / L to thisAdd 0.5 g of a solution of ethylmagnesium bromide in tetrahydrofuran (manufactured by Tokyo Chemical Industry Co., Ltd.),Water in the system was removed.continue,0.44 g (0.004 mol; Wako Pure Chemical Industries, Ltd.) of ethyl bromide was added.Stir for a while,It was confirmed that a fever occurred.Then, 45.0 g (0.2 mol;Wako Pure Chemical Industries, Ltd.) was gradually dropped.After the dripping endWhile stirring at 35 ° C. for 3 hoursAfter ripening, 13.5 g of toluene (0.3 times by weight / m-bromobenzotrifluoride: manufactured by Wako Pure Chemical Industries, Ltd.) is introduced.A Grignard reagent solution was obtained.next,19.8 g (0.2 mol; Wako Pure Chemical Industries, Ltd.) of acetic anhydride,Charge 54.0 g of toluene (1.2 times by weight / m-bromobenzotrifluoride: manufactured by Wako Pure Chemical Industries, Ltd.) into a four-necked flask (200 ml) with a thermometer,While replacing the system with nitrogen,Stir in a -15 ° C cooling bath.The Grignard reagent solution was added dropwise thereto while controlling the temperature of the reaction solution to -10 ° C to -5 ° C.After dripping the whole Grignard reagent solution, it stirred at room temperature for 2 hours.After completion of the stirring, the reaction solution was cooled to room temperature, and 51.3 g of a 12.2% aqueous hydrogen chloride solution was gradually added dropwise in a water bath. After dripping, the hydrolysis was completed by stirring for 1 hour. After the hydrolysis, stop the stirring, and let it stand still.3 '-trifluoromethyl acetophenoneAn oil phase containing is obtained.The obtained oil phase was analyzed by gas chromatography (GC). As a result, the reaction yield of 3'-trifluoromethylacetophenone was 81.3% (based on the starting material m-bromobenzotrifluoride). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With iodine; In dimethyl sulfoxide; at 20 - 110℃; for 2h; | Dissolve 3mL of m-trifluoromethylacetophenone in 10mLIn DMSO,Slowly add 2.5g iodine,Add 3.3g at room temperature with stirring<strong>[16313-65-8]<strong>[16313-65-8]2-Amino-5-nitrobenzamid</strong>e</strong> dissolved in 20mLa solution of DMSO,The reaction was carried out at 110 C for 2 h.The reaction system was added with 150 mL of water.Extracted with (3 x 60 mL) ethyl acetate.Reuse (2 × 40mL)Washing with saturated NaHSO3 solution to remove iodine,After washing with water, dry with anhydrous magnesium sulfate,Evaporate the solvent under reduced pressure.The residue was separated on a chromatographic column (eluent: ethyl acetate: petroleum ether = 1:2).2-(3-trifluoromethylbenzoyl)-6-nitro-4(3H)-quinazolinone 4.1 g,Yield 63%,Melting point 172-175 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With iodine; dimethyl sulfoxide In water at 80℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With piperidine; In ethanol; at 70℃; | General procedure: In an RB flask, 1H-indole-3-carboxaldehyde (1 mmol) andappropriate acetophenones (1.2 mmol) were taken and 5 ml ofethanol and 5 drops of piperidine were added. The resulting solutionwas then refluxed at 70 C and TLC was used to track the reactionprogress. Upon accomplishement of the reaction, thereaction mixture was transferred into cold water and furtherneutralized utilizing 1 N hydrochloric acid. The crude precipitateformed was filtered out, dried and recrystallized from chloroform.All the indole chalcones (1 to 25) were characterized using spectraltechniques and the spectral data are listed in the supplementarydata. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With manganese(II) bromide; water; lithium perchlorate; copper dichloride In acetonitrile at 60℃; for 8h; Sealed tube; Inert atmosphere; Electrochemical reaction; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: 3'-(trifluoromethyl)acetophenone With potassium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: With triethyl borane In tetrahydrofuran at 15 - 20℃; for 0.5h; Inert atmosphere; Stage #3: allyl bromide In tetrahydrofuran at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate In acetonitrile at 60℃; for 24h; Inert atmosphere; Darkness; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With sulphur In lithium hydroxide monohydrate; dimethyl sulfoxide at 95℃; for 6h; Green chemistry; | General procedure for 2-amino-4-arylthiazoles synthesis General procedure: A mixture of aromatic methyl keones (1 mmol), 50 wt% aqueous cyanamide solution (1275 mg, 15 mmol) and sulfur powder (64 mg, 2 mmol) in DMSO (1 mL) was stirred at 95 °C for 6 h. After the completion of reaction, it was cooled to room temperature and was treated with H2O (20 mL) and extracted with EtOAc (20 mL × 3). The combined organic layer was dried over anhydrous Na2SO4, concentrated, and purified through silica gel column chromatography to afford the substrates 3a-q. |
Tags: 349-76-8 synthesis path| 349-76-8 SDS| 349-76-8 COA| 349-76-8 purity| 349-76-8 application| 349-76-8 NMR| 349-76-8 COA| 349-76-8 structure
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